Chinese Journal of Applied Chemistry ›› 2018, Vol. 35 ›› Issue (9): 1037-1056.DOI: 10.11944/j.issn.1000-0518.2018.09.180173

• Review • Previous Articles     Next Articles

Research Progress on Asymmetric Synthesis of Donor-Acceptor Cyclopropanes and Their Enantioselective Ring-Opening/Annulation Reactions

WANG Lijiaa*(),TANG Yongab   

  1. aThe State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032,China
    bCollaborative Innovation Center of Chemical Science and Engineering,Tianjin 300072,China
  • Received:2018-05-14 Accepted:2018-05-31 Online:2018-09-01 Published:2018-08-06
  • Contact: WANG Lijia
  • Supported by:
    Supported by the National Natural Science Foundation of China(No.21432011, No.21772224), the National Basic Research Program of China(973 Program)(No.2015CB856600), the Key Research Program of Frontier Sciences of Chinese Academy of Sciences(No.QYZDY-SSW-SLH016), the Strategic Priority Research Program of the Chinese Academy of Sciences(No.XDB20000000), the Natural Science Foundation of Shanghai(No.17ZR1436900)

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