Lithium 2,3-dihydro-1-benzothiophene-1,1-dioxide: synthesis, characterization, DFT calculations and reactivity towards aldehydes and azometines

CADONI, ENZO;ARCA, MASSIMILIANO;DE MONTIS S;FATTUONI, CLAUDIA;PERRA E;CABIDDU, MARIA GRAZIA;USAI M;CABIDDU S.

2007-01-01

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Abstract

The sulfonyl carbanion derived from 2,3-dihydro-1-benzothiophene-1,1-dioxide and its lithium salt has been investigated by DFT calculations. NMR and IR spectroscopic analyses showed that the lithium sulfonyl carbanion exists in solution as a monomer in equilibrium with a dimer. The lithium carbanion was treated with aldehydes and azomethynes to give chiral hydroxy and amino derivatives. The stereochemistry of the products and the diastereoselectivity of the reaction were investigated