학술논문
Diastereoselective Addition of Enantiopure Lithium tert-Butylsulfinylferrocene to Imines.
Document Type
Article
Author
Source
Subject
*LITHIUM
*IMINES
*CHEMICAL reactions
*STEREOCHEMISTRY
*STATISTICAL correlation
*ORGANIC chemistry research
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Language
ISSN
0022-3263
Abstract
(S)-tert-Butylsulfinylferrocene was submitted to ortho-metalation, and the corresponding lithium derivative was trapped by alkyl or aryl imines bearing various electron-withdrawing groups on the nitrogen atom (Ts, Dpp, Boc). New aminosulfoxides were obtained with complete diastereocontrol when Dpp or Boc groups were used. The absolute configuration (SS,SFc,S) has been determined by single-crystal X-ray analysis and chemical correlation. An unusual pseudocyclic boatlike transition state has been proposed to explain the stereochemical course of this reaction. [ABSTRACT FROM AUTHOR]