Privileged chiral catalysts in asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reaction  

作　　者：WEI Yin SHI Min 

机构地区：[1]State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

出　　处：《Chinese Science Bulletin》2010年第17期1699-1711,共13页

基　　金：supported by Shanghai Municipal Committee of Science and Technology (06XD14005 and 08dj1400100-2);National Basic Research Program of China (2009CB825300);the National Natural Science Foundation of China (20872162, 20672127, 20821002 and 20732008)

摘　　要：In the past decade, the asymmetric Morita-Baylis-Hillman (MBH)/aza-Morita-Baylis-Hillman (aza-MBH) reaction has attracted great attention because it leads to the formation of densely functionalized products in a catalytic and atom-economic way. The MBH/aza-MBH adducts can be further applied in a wide variety of organic synthesis, such as peptide synthesis and heterocyclic compounds synthesis. After a lot of attempts to improve the enantioselectivity, many types of chiral organocatalysts have been identified as highly enantioselective organocatalysts in MBH/aza-MBH reaction. Especially, certain "privileged chiral catalysts" are highly enantioselective in MBH/aza-MBH reaction, which are designed and developed through introducing bi-/multi-functional groups on the so-called "privileged structures" such as cinchona alkaloids, BINAP/BINOL. This review summarizes the exciting advances about the design and development of chiral catalysts derived from "privileged structures" and their applications in asymmetric MBH/aza-MBH reaction.In the past decade, the asymmetric Morita-Baylis-Hillman （MBH）/aza-Morita-Baylis-Hillman （aza-MBH） reaction has attracted great attention because it leads to the formation of densely functionalized products in a catalytic and atom-economic way. The MBH/aza-MBH adducts can be further applied in a wide variety of organic synthesis, such as peptide synthesis and heterocyclic compounds synthesis. After a lot of attempts to improve the enantioselectivity, many types of chiral organocatalysts have been identified as highly enantioselective organocatalysts in MBH/aza-MBH reaction. Especially, certain ＂privileged chiral catalysts＂ are highly enantioselective in MBH/aza-MBH reaction, which are designed and developed through introducing hi-/multi-functional groups on the so-called ＂privileged structures＂ such as cinchona alkaloids, BINAP/BINOL. This review summarizes the exciting advances about the design and development of chiral catalysts derived from ＂privileged structures＂ and their applications in asymmetric MBH/aza-MBH reaction.

关 键 词：手性催化剂 选择性反应 不对称 氮杂 特权 对映选择性 有机催化剂 有机合成 

分 类 号：O643.32[理学—物理化学]