Tetrahedron

3-Bromo-2-t-butylsulfonyl-1-propene. a versatile multi-coupling reagent part 1

P Auvray, P Knochel, JF Normant

Index: Auvray, P.; Knochel, P.; Normant, J.F. Tetrahedron, 1988 , vol. 44, # 14 p. 4495 - 4508

Full Text: HTML

Citation Number: 30

Abstract

The 3-bromo-2-t-butylsulfonyl-1-propene 3 was prepared in two steps from allyl-t- butylthioether in 70% overall yield. This reagent reacts selectively with a broad range of nucleophiles (amine, thiolate, lithium ester-and keto-enolates, magnesium, zinc and lithium organomatallics) to furnish the unsaturated sulfones of type 4 in typical yields of 80–90%. The sulfone 3 reacts also in the presence of zinc with various electrophiles (aldehydes, ...