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Construction of Consecutive Chiral Non‐Racemic Quaternary and Tertiary Carbon Centers: A Short Synthetic Route to (−)‐Acetomycin
Author(s) -
Uenishi Jun′ichi,
Kawatsura Motoi,
Ikeda Daiji,
Muraoka Nobuhiro
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300504
Subject(s) - chemistry , enol , quaternary carbon , ligand (biochemistry) , nucleophilic substitution , stereochemistry , double bond , enantioselective synthesis , medicinal chemistry , nucleophile , organic chemistry , catalysis , receptor , biochemistry
Regio‐ and diastereoselective nucleophilic substitution of 2‐methylacetoacetate with a chiral non‐racemic π‐allyl Pd complex creates consecutive chiral non‐racemic quaternary and tertiary carbon centers. σ‐Bond formation between the re ‐face of the π‐allyl Pd complex and the re ‐face of the enol acetoacetate was controlled by the o ‐(diphenylphosphanyl)arylcarboxylic acid ligand selectively. (−)‐Acetomycin was synthesized in seven steps using this key approach. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)