Synthesis 2003(9): 1324-1328
DOI: 10.1055/s-2003-40210
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Generation of Alkenes and Dienes from Tosylates

Prodeep Phukan, Matthias Bauer, Martin E. Maier*
Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany
Fax: +49(7071)295137; e-Mail: martin.e.maier@uni-tuebingen.de;
Further Information

Publication History

Received 6 March 2003
Publication Date:
24 June 2003 (online)

Abstract

Several aldol products resulting from Evans aldol reactions were converted to primary alcohols. After conversion to the corresponding tosylates, heating with NaI and DBU in dimethoxyethane (glyme) effected clean elimination to the terminal olefin. This simple one-pot procedure was applied to other tosylates and a tosylate derived from a homoallylic alcohol. The latter gave rise to a diene.

20

Phukan P.; Sasmal, S.; Maier, M. E. Eur. J. Org. Chem. 2003, 1733.