Reactivity of lithium 2,3-dihydro-1-benzothiophene-1-oxide toward aldehydes and imines and DFT calculations |
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| Authors: | Enzo Cadoni Massimiliano Arca Claudia Fattuoni Maria G. Cabiddu Salvatore Cabiddu |
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| Affiliation: | a Dipartimento di Scienze Chimiche, Università degli Studi di Cagliari, Cittadella Universitaria di Monserrato, S.S. 554 Bivio per Sestu, I-09042 Monserrato, Italy
b Dipartimento di Chimica Inorganica ed Analitica, Università degli Studi di Cagliari, Cittadella Universitaria di Monserrato, S.S. 554 Bivio per Sestu, I-09042 Monserrato, Italy |
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| 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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| Keywords: | Metalation Carbanions Cyclic sulfoxide Density Functional Theory calculations Sulfur heterocycles |
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