Origins of stereoselectivity in radical additions: reactions of alkenes and radicals bearing oxazolidine and thiazolidine amide groups

…, IJ Rosenstein, RA Breyer, JD Bruhnke…

Index: Porter, Ned A.; Rosenstein, Ian J.; Breyer, Robert A.; Bruhnke, John D.; Wu, Wen-Xue; McPhail, Andrew T. Journal of the American Chemical Society, 1992 , vol. 114, # 20 p. 7664 - 7676

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Citation Number: 51

Abstract

Abstract: Single-crystal X-ray analysis of four alkenes that undergo stereoselective radical addition reactions are reported. The facial selectivity of radical additions to these alkenes is understood based upon their solid-state conformations. Alkenes which have a conformation placing a group at a position in space sterically protecting one of the faces from addition undergo radical addition with diastereofacial selectivity. The structures of the alkenes are ...

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