Stereoselective Synthesis of Z-α,β-Unsaturated Sulfones Using Peterson Reagents

被引：17

作者：

Ando, Kaori ^{[1
]}

Wada, Tomohiro ^{[1
]}

Okumura, Miho ^{[1
]}

Sumida, Hiroshi ^{[1
]}

机构：

[1] Gifu Univ, Dept Chem & Biomol Sci, Fac Engn, Gifu 5011193, Japan

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 24期

关键词：

ASYMMETRIC CONJUGATE ADDITION; VINYL SULFONES; AGENTS; ALPHA;

D O I：

10.1021/acs.orglett.5b03008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New Peterson reagents were prepared by introducing alkyloxy groups on the silicon atom in order to fix the conformation of the sulfone anion. The reagents 1d and 1e reacted with a variety of aldehydes after the treatment with Li-base to give Z-alpha,beta-unsaturated sulfones with up to >99:1 selectivity in good to excellent yields. For the reaction with aliphatic aldehydes, CPME (cyclopentyl methyl ether) is the choice of solvent, while DME (1,2-dimethoxyethane) gave higher selectivity for the reaction with aromatic aldehydes.

引用

页码：6026 / 6029

页数：4

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