Preparation of New Chiral Building Blocks by a Mukaiyama-Michael Reaction of 2-(Phenylsulfonyl)cyclopent-2-en-1-one

被引：0

作者：

Sugiyama, Ryoji ^{[1
]}

Nakada, Masahisa ^{[1
]}

机构：

[1] Waseda Univ, Sch Adv Sci & Engn, Dept Chem & Biochem, 3-4-1 Ohkubo,Shinjuku Ku, Tokyo 1698555, Japan

来源：

SYNLETT | 2023年 / 34卷 / 11期

关键词：

Mukaiyama-Michael reaction; asymmetric catalysis; enantioselectivity; diastereoselectivity; chiral building blocks; phenylsulfones; SILYLKETENE ACETALS; CYTOTOXICITY; COMPLEXES; ADDITIONS; ETHERS;

D O I：

10.1055/a-2030-7082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly enantio-and diastereoselective Mukaiyama- Michael reaction of 2-(phenylsulfonyl)cyclopent-2-en-1-one by using an enol silane of tert-butyl thiopropionate is described. The product was formed in 87% yield with a dr of 27:1 and 91% ee under stoichiometric conditions, whereas the yield, dr, and ee were 89%, 49:1, and 88% ee, respectively, under catalytic conditions. A highly stereoselective epimerization of the product of the Mukaiyama-Michael reaction which proceeds in 77% yield with a dr of 22:1 is also described. Because both enantiomers of the ligand for this Mukaiyama-Michael reaction are available, a method for the synthesis of all four stereoisomers of the product as useful chiral building blocks has been established.

引用

页码：1235 / 1240

页数：6

共 10 条

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