A Study of Samarium(II)-Water Allylic Benzoate Reductions

Chelation and Stereodirecting Group Effects on Regio- and Diastereoselective Samarium(II)-Water Allylic Benzoate Reductions: T. F. Stockdale, M. A. Leitch, G. W. O’Neil
Synthesis 2020, 52, DOI: 10.1055/s-0039-1690826


Samarium(II) iodide is a very versatile reducing agent in organic synthesis. Its reach chemistry can be modulated using a variety of experimental factors, including additives, which can be used to fine-tune the reductions outcome. Recently, the group of Professor Gregory O’Neil from the Western Washington University (Bellingham, USA) has reported a detailed study of the SmI2(H2O)n-promoted reduction of allylic benzoates carrying chelating groups, such as hydroxyls, and the influence on regio- and stereoselectivity of different stereodirecting groups present on the substrates backbone. High yields of the corresponding deoxybenzoylated carbinols were obtained in all cases, together with very good regio-/stereocontrol.

Professor O’Neil said: “We think this reaction represents a highly versatile and accessible method for stereoselective asymmetric carbon atom synthesis.“

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