Tetrahedron letters

Ring opening of 2, 3-epoxy 1-tosylates to halohydrins and subsequent elaboration to asymmetrical alcohols

C Federici, G Righi, L Rossi, C Bonini, L Chiummiento…

Index: Federici; Federici, Chiara; Righi; Righi, Giuliana; Rossi; Rossi, Leucio; Bonini; Bonini, Carlo; Chiummiento; Chiummiento, Lucia; Funicello; Funicello, Maria Tetrahedron Letters, 1994 , vol. 35, # 5 p. 797 - 800

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Citation Number: 18

Abstract

Abstract 2, 3-epoxy alcohols-1-tosylates are regio and chemoselectively opened to the corresponding 3-halohydrins (I, Br, Cl): the reduction of the iodohydrins to the monoprotected diols and subsequent standard coupling of the tosyl group leads to a straightforward synthesis of optically active naturally occurring pheromones.