Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5224724 | Tetrahedron | 2008 | 9 Pages |
Abstract
The sulfinyl carbanion derived from 2,3-dihydro-1-benzothiophene-1-oxide and its lithium salt has been investigated by DFT calculations. The lithium carbanion was treated with aldehydes and imines to give chiral hydroxy and amino derivatives, with high stereoselectivity at the carbon α to the sulfoxide group (trans diastereoisomers), but with low diastereoselectivity at the hydroxyl or amine group. DFT calculations were used to rationalize the different stereochemical behavior of cyclic and acyclic lithiated sulfoxides in the reaction with aldehydes and azomethines.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Enzo Cadoni, Massimiliano Arca, Michele Usai, Claudia Fattuoni, Efisio Perra, Maria G. Cabiddu, Stefania De Montis, Salvatore Cabiddu,