Novel approach to the synthesis of enantioenriched sulfoxides. Highly diastereoselective alkylation of sulfenate anions with 1,4-asymmetric induction

被引：38
作者：
Sandrinelli, F
Perrio, S
Averbuch-Pouchot, MT
机构：
[1] Univ Caen, ISMRA, Lab Chim Mol & Thioorgan, UMR CNRS 6507, F-14050 Caen, France
[2] Univ Grenoble 1, LEDSS, UMR CNRS 5616, F-38041 Grenoble 9, France
来源：
ORGANIC LETTERS | 2002年 / 4卷 / 21期
关键词：
D O I：
10.1021/ol026563s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] Efficient 1,4-asymmetric induction with an enantiopure aminoalkyl group as the chiral auxiliary has been achieved in the first example of diastereoselective alkylation (up to 98:2) of a sulfenate anion, readily prepared by oxidation of the corresponding thiolate. The stereochemistry of the sulfoxide produced is the opposite of that obtained by the conventional route based on oxidation of the sulfide precursor.
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页码：3619 / 3622
页数：4
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