A new synthesis of α, β-unsaturated sulphonates and their stereoselective conversion into trans-α, β-epoxysulphonates

JC Carretero, L Ghosez

Index: Carretero, Juan Carlos; Ghosez, Leon Tetrahedron Letters, 1987 , vol. 28, # 10 p. 1101 - 1104

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Citation Number: 10

Abstract

The method is quite general (Table 1). Yields are good even in the case of enolizable or hindered carbonyl compounds. Poor stereoselectivities were observed except with aromatic (3d-3f) or hindered(3~) carbonyl coumpounds which gave predominantly the (E! isomer.--- Addition of HMPA (5 equiv.) or TMEDA (2 equiv.) as cosolvent did not modify significantly the E: Z ratio. However a significant improvement of stereoselectivity in favour of the (E) ...