Ring-Opening Regio-, Diastereo-, and Enantioselective 1,3 Chlorochalcoge nation of Cyclopropyl Carbaldehydes

被引：64
|
作者：
Wallbaum, Jan [1 ]
Garve, Lennart K. B. [1 ]
Jones, Peter G. [2 ]
Werz, Daniel B. [1 ]
机构：
[1] Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ Chem, Hagenring 30, D-38106 Braunschweig, Germany
[2] Tech Univ Carolo Wilhelmina Braunschweig, Inst Inorgan & Analyt Chem, Hagenring 30, D-38106 Braunschweig, Germany
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 52期
基金：
欧洲研究理事会;
关键词：
1,3-bisfunctionalization; cyclopropane; enantioselectivity; organocatalysis; sulfur; DONOR-ACCEPTOR CYCLOPROPANES; DIELS-ALDER REACTION; CYCLOADDITION REACTIONS; ORGANIC CATALYSIS; ENAMINE CATALYSIS; ALPHA; BETA-UNSATURATED ALDEHYDES; 1,3-DIPOLAR CYCLOADDITION; SULFENYL CHLORIDES; ALPHA-ALKYLATION; PHENYL SELENIDE;
D O I：
10.1002/chem.201605265
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
meso-Cyclopropyl carbaldehydes are treated in the presence of an organocatalyst with sulfenyl and selenyl chlorides to afford 1,3chlorochal cogenated products. The transformation is achieved by a merged iminium-enamine activation. The enantioselective desymmetrization reaction, leading to three adjacent stereocenters, furnished the target products in complete regioselectivity and moderate to high diastereo- and enantioselectivities (d.r. up to 15:1 and e.r. up to 93:7).
引用
收藏
页码：18756 / 18759
页数：4
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