Tetrahedron Letters

High-speed microwave-promoted Mitsunobu inversions. Application toward the deracemization of sulcatol

A Steinreiber, A Stadler, SF Mayer, K Faber…

Index: Steinreiber, Andreas; Stadler, Alexander; Mayer, Sandra F; Faber, Kurt; Kappe Tetrahedron Letters, 2001 , vol. 42, # 36 p. 6283 - 6286

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Citation Number: 44

Abstract

An enantioconvergent synthesis of the aggregation pheromones (R)-and (S)-sulcatol (6- methyl-5-hepten-2-ol) is described. Key steps in the deracemization strategy are sequential combinations of enzymatic resolutions and Mitsunobu inversions. Racemization-free Mitsunobu transformations have been carried out within 5 min by microwave irradiation, providing the desired sulcatyl acetates with clean inversion of chirality.