Generation and Reactivity of Oxazolidinone Derived N-Acyl Radicals

Gary E. Keck; Mark C. Grier

doi:10.1055/s-1999-2913

Synlett 1999; 1999(10): 1657-1659
DOI: 10.1055/s-1999-2913

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Generation and Reactivity of Oxazolidinone Derived N-Acyl Radicals

Gary E. Keck^* , Mark C. Grier

^*Department of Chemistry, University of Utah, Salt Lake City, Utah 84112, USA; Fax + 1(8 01)5 81-70 55; E-mail: keck@chemistry.utah.edu

Abstract

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The N-acyl(phenylseleno)oxazolidinone 5 was prepared (85% yield) by treatment of the lithium salt of oxazolidinone with triphosgene, followed by addition of benzeneselenol. Reduction of 5 with n-Bu₃SnH/AIBN gave the N-formyloxazolidinone 6 (99%) and reaction with allyltri-n-butylstannane gave 7 (89%). Bimolecular additions to various alkenes using the N-acyl radical derived from oxazolidinone 5 were also studied. Best results were obtained with electron rich olefins, such as enol ether derivatives. Eight such additions are reported, with yields ranging from 51-90%. Two prochiral substrates showed significant levels of diastereoselectivity in reactions with 5/Bu₃SnH.

radicals - radical reactions - acylations - stereoselectivity - Lewis acids

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