推-拉电子体系环丙烷的不对称合成及其对映选择性开环/环化反应研究进展

doi:10.11944/j.issn.1000-0518.2018.09.180173

摘要/Abstract

摘要：

含有推-拉电子(DA)体系的张力环化合物,例如DA环丙烷,是非常有用的合成砌块,被应用于天然产物全合成以及合成具有生物活性的分子的研究中。近年来,本课题组利用手性铜、镍等配合物为催化剂,一方面发展了一系列高效合成手性DA环丙烷的新方法;另一方面陆续实现了仲胺、醇、硝酮、氮杂亚胺叶立德、烯醇硅醚、吲哚等多种亲核试剂与DA环丙烷的高对映选择性开环/环化反应。本文结合我们课题组工作综述了DA环丙烷化合物的不对称合成、开环/环化反应以及动力学拆分方面的主要研究进展并进行了展望。

关键词: 环丙烷, 环丙烷化, 开环, 环化, 对映选择性

Abstract:

Donor acceptor(DA) strained ring compounds, such as DA cyclopropanes, are useful synthetic building blocks, which have been applied in the total synthesis of natural products and biologically active molecules. Recent years, we have developed a series of highly effective methods for the preparation of chiral DA cyclopropanes, as well as the enantioselective ring-opening and annulation reactions of DA cyclopropanes with nucleophiles, such as amines, alcohols, nitrones, azomethine imines, enol silyl ethers, indoles and so on, by employing chiral copper or nickel complexes as catalysts. This accounts summarized our studies on the enantioselective cyclopropanation, asymmetric ring-opening/annulation and kinetic resolution of racemic DA cyclopropanes.

Key words: cyclopropanes, cyclopropanation, ring-opening, annulation, enantioselectivity

王丽佳,唐勇. 推-拉电子体系环丙烷的不对称合成及其对映选择性开环/环化反应研究进展[J]. 应用化学, 2018, 35(9): 1037-1056.

WANG Lijia,TANG Yong. Research Progress on Asymmetric Synthesis of Donor-Acceptor Cyclopropanes and Their Enantioselective Ring-Opening/Annulation Reactions[J]. Chinese Journal of Applied Chemistry, 2018, 35(9): 1037-1056.

参考文献

[1]	Danishefsky S.Electrophilic Cyclopropanes in Organic Synthesis[J]. Acc Chem Res,1979,12(2):66-72.
[2]	Reissig H U.Donor-Acceptor-Substituted Cyclopropanes-Versatile Building-Blocks in Organic-Synthesis[J]. Top Curr Chem,1988,144:73-135.
[3]	Yu M,Pagenkopf B L.Recent Advances in Donor-Acceptor(DA) Cyclopropanes[J]. Tetrahedron,2005,61(2):321-347.
[4]	Waser J,De Simone F.Cyclization and Cycloaddition Reactions of Cyclopropyl Carbonyls and Imines[J]. Synthesis,2009,(20):3353-3374.
[5]	Mel'nikov M Y,Budynina E M,Ivanova O A,et al. Recent Advances in Ring-Forming Reactions of Donor Acceptor Cyclopropanes[J]. Mendeleev Commun,2011,21(6):293-301.
[6]	Schneider T F,Kaschel J,Werz D B.A New Golden Age for Donor-Acceptor Cyclopropanes[J]. Angew Chem Int Ed,2014,53(22):5504-5523.
[7]	Grover H K,Emmett M R,Kerr M A.Carbocycles from Donor-Acceptor Cyclopropanes[J]. Org Biomol Chem,2015,13(3):655-671.
[8]	Lebel H,Marcoux J F,Molinaro C,et al. Stereoselective Cyclopropanation Reactions[J]. Chem Rev,2003,103(4):977-1050.
[9]	Muller P.Asymmetric Transfer of Carbenes with Phenyliodonium Ylides[J]. Acc Chem Res,2004,37(4):243-251.
[10]	Pellissier H.Recent Developments in Asymmetric Cyclopropanation[J]. Tetrahedron,2008,64(30/31):7041-7095.
[11]	Pfaltz A. Comprehensive Asymmetric Catalysis[M]. Jacobsen E N,Pflatz A,Yamamoto H,Eds. Berlin:Springer-Verlag,1999,II:513.
[12]	Reissig H U,Zimmer R.Donor-acceptor-substituted Cyclopropane Derivatives and Their Application in Organic Synthesis[J]. Chem Rev,2003,103(4):1151-1196.
[13]	Carson C A,Kerr M A.Heterocycles from Cyclopropanes:Applications in Natural Product Synthesis[J]. Chem Soc Rev,2009,38(11):3051-3060.
[14]	Reissig H U,Zimmer R.Thrilling Strain- Donor-Acceptor-Substituted Cyclobutanes for the Synthesis of (Hetero)Cyclic Compounds[J]. Angew Chem Int Ed,2015,54(17):5009-5011.
[15]	Nozaki H,Moriuti S,Takaya H,et al, Asymmetric Induction in Carbenoid Reaction by Means of a Dissymmetric Copper Chelate[J]. Tetrahedron Lett,1966,(43):5239-5240.
[16]	Nozaki H,Takaya H,Moriuti S,et al. Homogeneous Catalysis in Decomposition of Diazo Compounds by Copper Chelates[J]. Tetrahedron,1968,24(9):3655-3656.
[17]	Fritschi H,Leutenegger U,Pfaltz A.Chiral Copper-Semicorrin Complexes as Enantioselective Catalysts for the Cyclopropanation of Olefins by Diazo Compounds[J]. Angew Chem Int Ed,1986,25(11):1005-1006.
[18]	Fritschi H,Leutenegger U,Siegmann K,et al. Semicorrin Metal Complexes as Enantioselective Catalysts.Part 1.Synthesis of Chiral Semicorrin Ligands and General Concepts[J]. Helv Chim Acta,1988,71(6):1541-1552.
[19]	Fritschi H,Leutenegger U,Pfaltz A.Semicorrin Metal Complexes as Enantioselective Catalysts.Part 2.Enantioselective Cyclopropane Formation from Olefins with Diazo Compounds Catalyzed by Chiral (Semicorrinato)Copper Complexes[J]. Helv Chim Acta,1988,71(6):1553-1565.
[20]	Doyle M P,Bagheri V,Wandless T J,et al. Exceptionally High Trans(Anti) Stereoselectivity in Catalytic Cyclopropanation Reactions[J]. J Am Chem Soc,1990,112(5):1906-1912.
[21]	Evans D A,Woerpel K A,Hinman M M,et al. Bis(oxazolines) as Chiral Ligands in Metal-Catalyzed Asymmetric Reactions. Catalytic, Asymmetric Cyclopropanation of Olefins[J]. J Am Chem Soc,1991,113(2):726-728.
[22]	Ito K,Katsuki T.Asymmetric Cyclopropanation of E-Oleflns Using a Copper Complex of an Optically Active Bipyridine as a Catalyst[J]. Synlett,1993,(9):638-640.
[23]	Suematsu H,Kanchiku S,Uchida T,et al. Construction of Aryliridium-Salen Complexes:Enantio- and Cis-Selective Cyclopropanation of Conjugated and Nonconjugated Olefins[J]. J Am Chem Soc,2008,130(31):10327-10337.
[24]	Nishimura T,Maeda Y,Hayashi T.Asymmetric Cyclopropanation of Alkenes with Dimethyl Diazomalonate Catalyzed by Chiral Diene-Rhodium Complexes[J]. Angew Chem Int Ed,2010,49(40):7324-7327.
[25]	Zhu S,Perman J A,Zhang X P.Acceptor/Acceptor-Substituted Diazo Reagents for Carbene Transfers:Cobalt-Catalyzed Asymmetric Z-Cyclopropanation of Alkenes with α-Nitrodiazoacetates[J]. Angew Chem Int Ed,2008,47(44):8460-8463.
[26]	Lindsay V N G,Nicolas C,Charette A B. Asymmetric Rh(Ⅱ)-Catalyzed Cyclopropanation of Alkenes with Diacceptor Diazo Compounds:p-Methoxyphenyl Ketone as a General Stereoselectivity Controlling Group[J]. J Am Chem Soc,2011,133(23):8972-8981.
[27]	M ller P,Ghanem A. Rh(Ⅱ)-Catalyzed Enantioselective Cyclopropanation of Olefins with Dimethyl Malonate via in Situ Generated Phenyliodonium Ylide[J]. Org Lett,2004,6(23):4347-4350.
[28]	Moreau B,Charette A B.Expedient Synthesis of Cyclopropane α-Amino Acids by the Catalytic Asymmetric Cyclopropanation of Alkenes Using Iodonium Ylides Derived from Methyl Nitroacetate[J]. J Am Chem Soc,2005,127(51):18014-18015.
[29]	Harrington P,Kerr M A.The High Pressure Reaction of Cyclopropanes with Indoles Catalyzed by Ytterbium Triflate[J]. Tetrahedron Lett,1997,38(34):5949-5952.
[30]	Sibi M P,Ma Z,Jasperse C P.Enantioselective Addition of Nitrones to Activated Cyclopropanes[J]. J Am Chem Soc,2005,127(16):5764-5765.
[31]	Parsons A T,Johnson J S.Catalytic Enantioselective Synthesis of Tetrahydrofurans:A Dynamic Kinetic Asymmetric [3+2] Cycloaddition of Racemic Cyclopropanes and Aldehydes[J]. J Am Chem Soc,2009,131(9):3122-3123.
[32]	Parsons A T,Smith A G,Neel A J,et al. Dynamic Kinetic Asymmetric Synthesis of Substituted Pyrrolidines from Racemic Cyclopropanes and Aldimines: Reaction Development and Mechanistic Insights[J]. J Am Chem Soc,2010,132(28):9688-9692.
[33]	Trost B M,Morris P J.Palladium-Catalyzed Diastereo- and Enantioselective Synthesis of Substituted Cyclopentanes Through a Dynamic Kinetic Asymmetric Formal [3+2]-Cycloaddition of Vinyl Cyclopropanes and Alkylidene Azlactones[J]. Angew Chem Int Ed,2011,50(27):6167-6170.
[34]	de Nanteuil F,Waser J. Catalytic [3+2] Annulation of Aminocyclopropanes for the Enantiospecific Synthesis of Cyclopentylamines[J]. Angew Chem Int Ed,2011,50(50):12075-12079.
[35]	de Nanteuil F,Serrano E,Perrotta D,et al. Dynamic Kinetic Asymmetric [3+2] Annulation Reactions of Aminocyclopropanes[J]. J Am Chem Soc,2014,136(17):6239-6242.
[36]	Hashimoto T,Kawamata Y,Maruoka K.An Organic Thiyl Radical Catalyst for Enantioselective Cyclization[J]. Nat Chem,2014,6(8):702-705.
[37]	Xia Y,Liu X H,Zheng H F,et al. Asymmetric Synthesis of 2,3-Dihydropyrroles by Ring-Opening/Cyclization of Cyclopropyl Ketones Using Primary Amines[J]. Angew Chem Int Ed,2015,54(1):227-230.
[38]	Xia Y,Lin L,Chang F,et al. Asymmetric Ring-Opening of Cyclopropyl Ketones with Thiol, Alcohol, and Carboxylic Acid Nucleophiles Catalyzed by a Chiral N,N'-Dioxide-Scandium(Ⅲ) Complex[J]. Angew Chem Int Ed,2015,54(46):13952-13956.
[39]	Xia Y,Lin L,Chang F,et al. Asymmetric Ring Opening/Cyclization/Retro-Mannich Reaction of Cyclopropyl Ketones with Aryl 1,2-Diamines for the Synthesis of Benzimidazole Derivatives[J]. Angew Chem Int Ed,2016,55(40):12228-12232.
[40]	Fu X,Lin L L,Xia Y,et al. Catalytic Asymmetric [3+3] Annulation of Cyclopropanes with Mercaptoacetaldehyde[J]. Org Biomol Chem,2016,14(25):5914-5917.
[41]	Liao S,Sun X L,Tang Y.Side Arm Strategy for Catalyst Design: Modifying Bisoxazolines for Remote Control of Enantioselection and Related[J]. Acc Chem Res,2014,47(8):2260-2272.
[42]	Wang L,Tang Y.Asymmetric Ring-Opening Reactions of Donor-Acceptor Cyclopropanes and Cyclobutanes[J]. Isr J Chem,2016,56(6/7):463-475.
[43]	Li J,Liao S H,Xiong H,et al. Highly Diastereo- and Enantioselective Cyclopropanation of 1,2-Disubstituted Alkenes[J]. Angew Chem Int Ed,2012,51(35):8838-8841.
[44]	Xu Z H,Zhu S N,Sun X L,et al. Sidearm Effects in the Enantioselective Cyclopropanation of Alkenes with Aryldiazoacetates Catalyzed by Trisoxazoline/Cu(Ⅰ)[J]. Chem Commun,2007,(19):1960-1962.
[45]	Deng C,Wang L J,Zhu J,et al. A Chiral Cagelike Copper(Ⅰ) Catalyst for the Highly Enantioselective Synthesis of 1,1-Cyclopropane Diesters[J]. Angew Chem Int Ed,2012,51(46):11620-11623.
[46]	Deng C,Liu H K,Zheng Z B,et al. Copper-Catalyzed Enantioselective Cyclopropanation of Internal Olefins with Diazomalonates[J]. Org Lett,2017,19(21):5717-5719.
[47]	Feng L W,Wang P,Wang L,et al. Copper(Ⅰ)/SaBOX Catalyzed Highly Diastereo- and Enantio-Selective Cyclopropanation of cis-1,2-Disubstituted Olefins with α-Nitrodiazoacetates[J]. Sci Bull,2014,60(2):210-215.
[48]	Zhou Y Y,Wang L J,Li J,et al. Side-Arm-Promoted Highly Enantioselective Ring-Opening Reactions and Kinetic Resolution of Donor-Acceptor Cyclopropanes with Amines[J]. J Am Chem Soc,2012,134(22):9066-9069.
[49]	Kang Q,Wang L,Zheng Z,et al. Sidearm as a Control in the Asymmetric Ring Opening Reaction of Donor-Acceptor Cyclopropane[J]. Chinese J Chem,2014,32(8):669-672.
[50]	Kang Q K,Wang L,Liu Q J,et al. Asymmetric H2O-Nucleophilic Ring Opening of D-A Cyclopropanes:Catalyst Serves as a Source of Water[J]. J Am Chem Soc,2015,137(46):14594-14597.
[51]	Fang J,Ren J,Wang Z W.Sc(OTf)3-Catalyzed Smooth Tandem [3+2] Cycloaddition/Ring Opening of Donor-Acceptor Cyclopropane 1,1-Diesters with Enol Silyl Ethers[J]. Tetrahedron Lett,2008,49(47):6659-6662.
[52]	Qu J P,Deng C,Zhou J,et al. Switchable Reactions of Cyclopropanes with Enol Silyl Ethers. Controllable Synthesis of Cyclopentanes and 1,6-Dicarbonyl Compounds[J]. J Org Chem,2009,74(20):7684-7689.
[53]	Qu J P,Liang Y,Xu H,et al. Highly Diastereoselective Construction of Fused Carbocycles from Cyclopropane-1,1-Dicarboxylates and Cyclic Enol Silyl Ethers:Scope, Mechanism, and Origin of Diastereoselectivity[J]. Chem Eur J,2012,18(8):2196-2201.
[54]	Xu H,Qu J P,Liao S,et al. Highly Enantioselective [3+2] Annulation of Cyclic Enol Silyl Ethers with Donor-Acceptor Cyclopropanes:Accessing 3a-Hydroxy [n.3.0]Carbobicycles[J]. Angew Chem Int Ed,2013,52(14):4004-4007.
[55]	Xu H,Hu J L,Wang L,et al. Asymmetric Annulation of Donor-Acceptor Cyclopropanes with Dienes[J]. J Am Chem Soc,015,137(25):8006-8009.
[56]	Chagarovskiy A O,Budynina E M,Ivanova O A,et al. Lewis Acid-catalyzed Reactions of Donor-Acceptor Cyclopropanes with Furan Derivatives[J]. Tetrahedron,2009,65:5385-5392.
[57]	Emmett M R,Kerr M A.Nucleophilic Ring Opening of Cyclopropane Hemimalonates Using Internal Bronsted Acid Activation[J]. Org Lett,2011,13(16):4180-4183.
[58]	Wales S M,Walker M M,Johnson J S.Asymmetric Synthesis of Indole Homo-Michael Adducts via Dynamic Kinetic Friedel-Crafts Alkylation with Cyclopropanes[J]. Org Lett,2013,15(10):2558-2561.
[59]	Xiong H,Xu H,Liao S,et al. Copper-Catalyzed Highly Enantioselective Cyclopentannulation of Indoles with Donor-Acceptor Cyclopropanes[J]. J Am Chem Soc,2013,135(21):7851-7854.
[60]	Zhu J,Liang Y,Wang L,et al. Remote Ester Groups Switch Selectivity: Diastereodivergent Synthesis of Tetracyclic Spiroindolines[J]. J Am Chem Soc,2014,136(19):6900-6903.
[61]	Liu Q J,Yan W G,Wang L,et al. One-Pot Catalytic Asymmetric Synthesis of Tetrahydrocarbazoles[J]. Org Lett,2015,17(16):4014-4017.
[62]	Grover H K,Lebold T P,Kerr M A.Tandem Cyclopropane Ring-Opening/Conia-ene Reactions of 2-Alkynyl Indoles:A [3+3] Annulative Route to Tetrahydrocarbazoles[J]. Org Lett,2011,13(2):220-223.
[63]	Talukdar R,Tiwari D P,Saha A,et al. Diastereoselective Synthesis of Functionalized Tetrahydrocarbazoles via a Domino-Ring Opening-Cyclization of Donor-Acceptor Cyclopropanes with Substituted 2-Vinylindoles[J]. Org Lett,2014,16(15):3954-3957.
[64]	Sherry B D,Furstner A.Iron-catalyzed Addition of Grignard Reagents to Activated Vinyl Cyclopropanes[J]. Chem Commun,2009,(46):7116-7118.
[65]	Xing S,Pan W,Liu C,et al. Efficient Construction of Oxa-and Aza-[n.2.1] Skeletons:Lewis Acid Catalyzed Intramolecular [3+2] Cycloaddition of Cyclopropane 1,1-Diesters with Carbonyls and Imines[J]. Angew Chem Int Ed,2010,49(18):3215-3218.
[66]	Smith A G,Slade M C,Johnson J S.Cyclopropane-Aldehyde Annulations at Quaternary Donor Sites:Stereoselective Access to Highly Substituted Tetrahydrofurans[J]. Org Lett,2011,13(8):1996-1999.
[67]	Yu Q,Ma S.Lewis Acid-Catalyzed Unexpected Selective C—C Bond Cleavage:An Efficient and Mild Construction of Cyclopentenes[J]. Chem Commun,2012,48(96):11784-11786.
[68]	Wenz D R,Read de Alaniz. Aza-Piancatelli Rearrangement Initiated by Ring Opening of Donor-Acceptor Cyclopropanes[J]. J Org Lett,2013,15(13):3250-3253.
[69]	Zhu W,Fang J,Liu Y,et al. Lewis Acid Catalyzed Formal Intramolecular [3+2] Cross-Cycloaddition of Cyclopropane 1,1-Diesters with Alkenes:General and Efficient Strategy for Construction of Bridged [n.2.1] Carbocyclic Skeletons[J]. Angew Chem Int Ed,2013,52(7):2032-2037.
[70]	Haubenreisser S,Hensenne P,Schröder S,et al. The Alkynyl Moiety as a Donor for Donor-Acceptor Cyclopropanes[J]. Org Lett,2013,15(9):2262-2265.
[71]	Mackay W D,Fistikci M,Carris R M,et al. Lewis Acid Catalyzed (3+2)-Annulations of Donor Acceptor Cyclopropanes and Ynamides[J]. Org Lett,2014,16(6):1626-1629.
[72]	YAN Wenguang,WANG Pan,WANG Lijia,et al. Copper Catalyzed [3+2] Annulation of Indoles with 1,1,2,2-Tetrasubstituted Donor-Acceptor Cyclopropanes[J]. Acta Chim Sin,2017,75(8):783-787(in Chinese). 严文广,王盼,王丽佳,等. 铜(Ⅱ)催化的吲哚与四取代DA环丙烷[3+2]开环/环化反应[J]. 化学学报,2017,75(8):783-787.
[73]	Kang Y B,Sun X L,Tang Y.Highly Enantioselective and Diastereoselective Cycloaddition of Cyclopropanes with Nitrones and Its Application in the Kinetic Resolution of 2-Substituted Cyclopropane-1,1-Dicarboxylates[J]. Angew Chem Int Ed,2007,46(21):3918-3921.
[74]	Zhou Y Y,Li J,Ling L,et al. Highly Enantioselective [3+3] Cycloaddition of Aromatic Azomethine Imines with Cyclopropanes Directed by π-π Stacking Interactions[J]. Angew Chem Int Ed,2013,52(5):1452-1456.
[75]	Liu Q S,Wang D Y,Yang Z J,et al. Ni-Al Bimetallic Catalyzed Enantioselective Cycloaddition of Cyclopropyl Carboxamide with Alkyne[J]. J Am Chem Soc,2017,139(50):18150-18153.