Limitations, mechanism and understanding of the origins of stereocontrol in (S)-dimethylsulfonium-(p-tolylsulfinyl)methylide-mediated epoxidation reactions

被引：9

作者：

Midura, Wanda H. ^{[1
]}

Cypryk, Marek ^{[1
]}

机构：

[1] Polish Acad Sci, Ctr Mol & Macromol Studies, PL-90363 Lodz Sienkiewicza 112, Poland

来源：

TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 02期

关键词：

CARBON BOND-FORMATION; ASYMMETRIC-SYNTHESIS; CHIRAL AUXILIARY; SULFUR YLIDES; SULFOXIDES; EPOXIDES; CYCLOPROPANATION; SULFINYL; AZIRIDINATION; OLEFINATION;

D O I：

10.1016/j.tetasy.2010.01.012

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The reaction of the (S)-dimethylsulfonium-(p-tolylsulfinyl)methylide with aldehydes gave alpha,beta-epoxy sulfoxides with high enantioselectivity and diastereoselectivity dependent on the aldehyde. The mechanism of the 'model' reactions [ylide substituted with Me S(O) or Ph S(O) with MeCHO or PhCHO] has been studied in detail using density functional theory. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：177 / 186

页数：10

共 3 条

[1] Highly stereoselective aziridination of imines with (S)-dimethylsulfonium-(p-tolylsulfinyl)methylide
Midura, Wanda H.
TETRAHEDRON LETTERS, 2007, 48 (22) : 3907 - 3910
[2] Stereoselective cyclopropyl phosphonate formation using (S)-dimethylsulfonium-(p-tolylsulfinyl)methylide. Unusual phosphoryl group migration
Midura, Wanda H.
Sobczak, Agata
Paluch, Piotr
TETRAHEDRON LETTERS, 2013, 54 (03) : 223 - 226
[3] Remote stereocontrol by the sulfinyl group:: Mukaiyama aldol reactions of (S)-2-[2-(p-tolylsulfinyl)phenyl]acetaldehyde in the asymmetric synthesis of β-hydroxyacids and 1,3-diols
Ruano, Jose L. Garcia
Fernandez-Ibanez, M. Angeles
Maestro, M. Carmen
TETRAHEDRON, 2006, 62 (52) : 12297 - 12305

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