铑催化不对称氢化2-苯基-2-丙烯醇合成手性2-苯基丙醇

doi:10.3724/SP.J.1095.2014.40054

摘要/Abstract

摘要： 通过铑催化不对称催化氢化的方法，实现了2-苯基-2-丙烯醇的不对称催化氢化，对一系列单齿及双齿磷配体进行了筛选，在温和的条件下，以较高对映体选择性的合成了手性2-苯基丙醇，最高获得了70%的ee值。

关键词: 手性苯基丙醇, 铑（Ⅰ）配合物, 不对称催化氢化, 苯基丙烯醇, 手性磷配体

Abstract: Rhodium-catalyzed asymmetric hydrogenation of 2-phenylprop-2-en-1-ol was investigated for the first time. Enantioselective synthesis of chiral 2-phenylpropanol with up to 70% ee was achieved through screen on a series of monodentate ligands and bidentate ligands.

Key words: chiral phenylpropanol, Rh(Ⅰ) complex, asymmetric catalytic hydrogenation, phenylprop-en-ol, chiral phosphorus ligand

中图分类号:

O621

段正超, 王联芝, 屈桃李, 左晓宇, 胡向平, 郑卓. 铑催化不对称氢化2-苯基-2-丙烯醇合成手性2-苯基丙醇[J]. 应用化学, DOI: 10.3724/SP.J.1095.2014.40054.

DUAN Zhengchao1*, WANG Lianzhi1, QU Taoli1, ZUO Xiaoyu1, HU Xiangping2*, ZHENG Zhuo2. Enantioselective Synthesis of Chiral 2-Phenylpropanol via Rh-catalyzed Asymmetric Hydrogenation of 2-Phenylprop-2-en-1-ol[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2014.40054.

参考文献

[1] Abate A,Brenna E,Fuganti C,et al. Chirality and Fragrance Chemistry:Stereoisomers of the Commercial Chiral Odorants Muguesia and Pamplefleur[J]. J Org Chem,2005,70(4):1281-1290.

[2] Serra S. Lipase-mediated Resolution of Substituted 2-Aryl-propanols:Application to the Enantioselective Synthesis of Phenolic Sesquiterpenes[J]. Tetrahedron:Asymmetry,2011,22(6):619-628.

[3] Wipf P,Ribe S. Water/MAO Acceleration of the Zirconocene-Catalyzed Asymmetric Methylalumination of r-Olefins[J]. Org Lett,2000,2(12):1713-1716.

[4] Deerenberg S,Kamer P C J,van Leeuwen P W N M. New Chiral Phosphine-Phosphite Ligands in the Enantioselective Rhodium-Catalyzed Hydroformylation of Styrene[J]. Organometallics,2000,19(11):2065-2072.

[5] de Vries J G,Elsevier C J(Eds). The Handbook of Homogeneous Hydrogenation[D]. Wiley-VCH,Weinheim,Germany,2007,Vol.1.

[6] Coll M,Pamies O,Diegueza M. A Modular Furanoside Thioether-Phosphite/Phosphinite/Phosphine Ligand Library for Asymmetric Iridium-Catalyzed Hydrogenation of Minimally Functionalized Olefins: Scope and Limitations[J]. Adv Synth Catal,2013,355(1):143-160.

[7] Mazuela J,Norrby P O,Andersson P G,et al. Pyranoside Phosphite_Oxazoline Ligands for the Highly Versatile and Enantioselective Ir-Catalyzed Hydrogenation of Minimally Functionalized Olefins.A Combined Theoretical and Experimental Study[J]. J Am Chem Soc,2011,133(34):13634-13645.

[8] Kallstrom K,Hedberg C,Brandt P,et al. Rationally Designed Ligands for Asymmetric Iridium-Catalyzed Hydrogenation of Olefins[J]. J Am Chem Soc,2004,126(44):14308-14309.

[9] Zeng Q H,Hu X P,Duan Z C,et al. Unsymmetrical Ferrocenylethylamine-Derived Monophosphoramidites:Highly Efficient Chiral Ligands for Rh-Catalyzed Enantioselective Hydrogenation of Enamides and α-Dehydroamino Acid Derivatives[J]. J Org Chem,2006,71(1):393-396.

[10] Huang J D,Hu X P,Duan Z C,et al. Readily Available Phosphine-Phosphoramidite Ligands for Highly Efficient Rh-Catalyzed Enantioselective Hydrogenations[J]. Org Lett,2006,8(19):4367-4370.

[11] Hu X P,Zheng Z. Unsymmetrical Hybrid Ferrocene-Based Phosphine-Phosphoramidites:A New Class of Practical Ligands for Rh-Catalyzed Asymmetric Hydrogenation[J]. Org Lett,2004,6(20):3585-3588.

[12] Duboudin J G,Jousseaume B,Saux A. Reactifs de Grignard Vinyliques Fonctionnels:Ⅰ.Reactivite des Organomagnesiens vis-a-vis d′alcools Acetyleniques en Presence d′halogenures Cuivreux[J]. J Organomet Chem,1979,168(1):1-11.