Intramolecular asymmetric Heck reactions: evidence for dynamic kinetic resolution effects.
[reaction: see text] 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.
McDermott
Michael C
MC
Wolfson Materials and Catalysis Centre, School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich, UK.
Stephenson
G Richard
GR
Hughes
David L
DL
Walkington
Andrew J
AJ