Regio- and Diastereoselective Samarium-Mediated Allylic Benzoate ReductionsFinancial support from the National Science Foundation (CHE-1151492) is gratefully acknowledged.
Received: 01 June 2017
Accepted after revision: 19 June 2017
20 July 2017 (eFirst)
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.