The deoxygenation of sulfoxide mediated by the Ph3P/Lewis acid combination and the application to the kinetic resolution of racemic phosphines using optically active sulfoxide

被引：40

作者：

Kikuchi, S ^{[1
]}

Konishi, H ^{[1
]}

Hashimoto, Y ^{[1
]}

机构：

[1] Univ Tokyo, Sch Engn, Dept Chem & Biotechnol, Bunkyo Ku, Tokyo 1138656, Japan

来源：

TETRAHEDRON | 2005年 / 61卷 / 14期

关键词：

phosphine; Lewis acid; deoxygenation; kinetic resolution;

D O I：

10.1016/j.tet.2005.01.127

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It was found that the combination of Ph3P/TiCl4 was an effective promoter for the deoxygenation of sulfoxides and gave the corresponding sulfides in good yield (up to 97%) under mild conditions. This method was applied to the reaction between racemic phosphines and (R)-methyl p-tolyl sulfoxide, and it was found that the kinetic resolution was achieved in moderate selectivities. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3587 / 3591

页数：5

共 3 条

[1] A CONVENIENT SYNTHESIS OF ISOTELLURAZOLES VIA DEOXYGENATION OF ISOTELLURAZOLE Te-OXIDE OLIGOMERS BY USING A COMBINATION OF Ph3P/I2
Taneichi, Yusuke
Shimoda, Kazuaki
Korenaga, Toshinobu
HETEROCYCLES, 2017, 94 (10) : 1931 - 1939
[2] SYNTHESIS OF RACEMIC ALPHA-AMINO CARBOXAMIDES VIA LEWIS ACID-MEDIATED REACTIONS OF ALPHA-METHOXYGLYCINAMIDE DERIVATIVES WITH ALLYLSILANES - ENZYMATIC RESOLUTION TO OPTICALLY-ACTIVE ALPHA-AMINO-ACIDS
ROOS, EC
MOOIWEER, HH
HIEMSTRA, H
SPECKAMP, WN
KAPTEIN, B
BOESTEN, WHJ
KAMPHUIS, J
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25): : 6769 - 6778
[3] A highly asymmetric, Lewis acid-catalysed Diels-Alder reaction using optically active 2-(3-tolyl-p-sulfinyl)furyl alpha,beta-unsaturated ketones as a dienophile
Arai, Y
Masuda, T
Masaki, Y
Shiro, M
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (08): : 759 - 762

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