Synlett 2017; 28(17): 2267-2271
DOI: 10.1055/s-0036-1590831
letter
© Georg Thieme Verlag Stuttgart · New York

Regio- and Diastereoselective Samarium-Mediated Allylic Benzoate Reductions

Trevor F. Stockdale, Gregory W. O’Neil*
  • Department of Chemistry, Western Washington University, Bellingham, WA, USA   Email: oneilg@wwu.edu
Financial support from the National Science Foundation (CHE-1151492) is gratefully acknowledged.
Further Information

Publication History

Received: 01 June 2017

Accepted after revision: 19 June 2017

Publication Date:
20 July 2017 (eFirst)

Abstract

A regio- and diastereoselective samarium(II)-mediated reduction of allylic benzoates is described. Yields for the reactions are generally high with diastereoselectivities up to 90:10 and in some cases only a single regioisomer was obtained. The stereoselectivity of the reaction is proposed to arise from chelation of a hydroxyl-stereocenter and starting alkene geometry, with protonation occurring intramolecularly by samarium-bound water.

Supporting Information