Rearrangement of homoallylic alcohols induced by DAST.

Rearrangement of homoallylic alcohols induced by DAST.

Organic letters (2006-05-05)

Sophie Canova, Véronique Bellosta, Serge Mignani, Antony Bigot, Janine Cossy

ABSTRACT

[reaction: see text] Treatment of beta,gamma-unsaturated monoprotected 1,2-diols with diethylaminosulfur trifluoride (DAST) allows the stereoselective formation of beta,gamma-unsaturated aldehydes in good yields and with a good transfer of chirality.

MATERIALS

Product Number

Brand

Product Description

235253

Sigma-Aldrich

(Diethylamino)sulfur trifluoride, 95%

774642

Sigma-Aldrich

(Diethylamino)sulfur trifluoride solution, 1.0 M in dichloromethane