Synlett 2017; 28(17): 2320-2324
DOI: 10.1055/s-0036-1588485
letter
© Georg Thieme Verlag Stuttgart · New York

Ferrier Rearrangement of 1,2-Dihydropyrans with Organozinc Species in Toluene/n-Dibutyl Ether

Pauline Rabet, Simon Wagschal*, Sébastien Lemaire*
This work has received funding from the European Community’s Seventh Framework Programme (FP7/2007-2013) and EFPIA companies’ in kind contribution for the Innovative Medicine Initiative under Grant Agreement No. 115360 (Chemical manufacturing methods for the 21st century pharmaceutical industries, CHEM21).
Further Information

Publication History

Received: 27 May 2017

Accepted: 05 June 2017

Publication Date:
18 July 2017 (eFirst)

Abstract

Herein, we report the catalyst-free addition of organozinc species to glycal derivatives and dihydropyrans in a toluene/n-dibutyl ether solvent mixture via a Ferrier rearrangement at room temperature. This methodology requires only a slight excess of the nucleophile and leads preferentially to the C-glycoside α-anomer. Various 1,2-dihydropyrans were assessed with a range of nucleophiles (aryl, alkynyl, alkyl) yielding the desired C-glycosides in good yield and diastereoselectivity up to 20:1.