A regio- and diastereoselective samarium(II)-mediated reduction of allylic benzoates has been developed, capable of producing a range of differentially substituted asymmetric carbon atoms. Yields for the reactions are generally high, with up to 90:10 diastereoselectivities obtained and often only a single regioisomer produced. The absolute geometry of the newly formed stereocenter can be predicted based on ring strain energetics of a substrate-chelated organosamarium intermediate, with protonation occurring intramolecularly by samarium-bound water.

Asymmetric carbon atom synthesis by samarium (II)-water allylic benzoate reductions

2019 Fall National Meeting

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