Pd asymmetric allylic alkylation (AAA). A powerful synthetic tool

Chem Pharm Bull (Tokyo). 2002 Jan;50(1):1-14. doi: 10.1248/cpb.50.1.

Abstract

Palladium catalyzed asymmetric allylic alkylations represent a challenging problem because the mechanism of the reaction places the chiral environment distal to the bond breaking or making events responsible for the asymmetric induction. Furthermore, unlike virtually every other asymmetric process, many strategies can be employed for introduction of asymmetry and many different types of bonds can be formed. While over 100 different ligands have been designed, a family of ligands derived from 2-diphenylphosphinobenzoic or 1-naphthoic acid and chiral scalemic diamines have been successful in inducing excellent enantioselectivity by five different enantiodiscriminating events. These methods have already provided practical strategies towards numerous biological targets--some of which are adenosine and its enantiomer, aflatoxin B, aristeromycin, calanolide A and B, carbovir, cyclophellitol, ethambutol, galanthamine, mannostatin, neplanocin, phyllanthocin, sphingofungins E and F, tetraponaines, vigabatrin, and valienamine.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.
  • Review

MeSH terms

  • Alkylation
  • Allyl Compounds / chemical synthesis
  • Allyl Compounds / chemistry*
  • Catalysis
  • Ligands
  • Models, Chemical
  • Palladium / chemistry*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Allyl Compounds
  • Ligands
  • Palladium