Intramolecular asymmetric Heck reactions: Evidence for dynamic kinetic resolution effects

Michael C. McDermott, G. Richard Stephenson, David L. Hughes, Andrew J. Walkington

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)

Abstract

Enantioselectivity of the cyclization of 1 varies at different stages in the reaction. X-ray crystallography has shown that 1 exists as enantiomerically pure (M) and (P) chiral helical structures defined by the relative orientations of the arene, amide, and alkene. The relative rates of interconversion of the rotamers of 1 have been established, leading to mechanistic proposals to account for the variation of ee based on kinetic resolution effects.
Original languageEnglish
Pages (from-to)2917-2920
Number of pages4
JournalOrganic Letters
Volume8
Issue number14
DOIs
Publication statusPublished - 2006

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