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手性二肽衍生多功能鏻盐催化的丙二酸酯对查尔酮衍生物的对映选择性迈克尔加成。

Enantioselective Michael Addition of Malonates to Chalcone Derivatives Catalyzed by Dipeptide-derived Multifunctional Phosphonium Salts.

机构信息

Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.

出版信息

J Org Chem. 2016 Oct 21;81(20):9973-9982. doi: 10.1021/acs.joc.6b01752. Epub 2016 Oct 6.

Abstract

Highly enantioselective Michael addition of malonates to enones catalyzed by dipeptide-derived multifunctional phosphonium salts has been developed. The newly established catalytic system was characterized with its wide substrate scope featured with aliphatic aldehyde-derived enones and substituted malonates. The gram scale-up synthesis of adducts can also be successfully achieved under optimal conditions with both excellent yield and enantioselectivity.

摘要

已开发出由二肽衍生的多功能鏻盐催化的马来酸酯对烯酮的高对映选择性迈克尔加成。新建立的催化体系具有广泛的底物范围的特点,包括脂肪醛衍生的烯酮和取代的马来酸酯。在最佳条件下,通过克级规模合成也可以成功实现加合物的合成,并且产率和对映选择性都很高。

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