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

Authors
Steinreiber, A Stadler, A Mayer, SF Faber, K Kappe, CO
Citation
A. Steinreiber et al., High-speed microwave-promoted Mitsunobu inversions. Application toward thederacemization of sulcatol, TETRAHEDR L, 42(36), 2001, pp. 6283-6286
Citations number
30
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
36
Year of publication
2001
Pages
6283 - 6286
Database
ISI
SICI code
0040-4039(20010903)42:36<6283:HMMIAT>2.0.ZU;2-K
Abstract
An enantioconvergent synthesis of the aggregation pheromones (R)- and (S)-s uleatol (6-methyl-5-hepten-2-ol) is described. Key steps in the deracemizat ion strategy are sequential combinations of enzymatic resolutions and Mitsu nobu inversions. Racemization-free Mitsunobu transformations have been carr ied out within 5 min by microwave irradiation, providing the desired sulcat yl acetates with clean inversion of chirality. (C) 2001 Elsevier Science Lt d. All rights reserved.