Stereodivergent SN2@P Reactions of Borane Oxazaphospholidines: Experimental and Theoretical Studies

H. Zijlstra, T. Léon, A. de Cózar, C. Fonseca Guerra, D. Byrom, A. Riera, X. Verdaguer, F.M. Bickelhaupt

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

The stereodivergent ring-opening of 2-phenyl oxazaphospholidines with alkyl lithium reagents is reported. N-H oxazaphospholidines derived from both (+)-cis-1-amino-2-indanol and (-)-norephedrine provide inversion products in a highly stereoselective process. In contrast, N-Me oxazaphospholidines yield ring-opening products with retention of configuration at the P center, as previously reported by Jugé and co-workers. As a result, from a single amino alcohol auxiliary, both enantiomers of key P-stereogenic intermediates could be synthesized. Theoretical studies of ring-opening with model oxazaphospholidines at the DFT level have elucidated the streochemical course of this process. N-H substrates react in a single step via preferential backside S
Original languageEnglish
Pages (from-to)4483-4491
JournalJournal of the American Chemical Society
Volume2013
Issue number135
DOIs
Publication statusPublished - 2013

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