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Enantioselective Synthesis of 4‐Hydroxytetrahydropyridine Derivatives by Intramolecular Addition of Tertiary Enamides to Aldehydes
Author(s) -
Tong Shuo,
Wang DeXian,
Zhao Liang,
Zhu Jieping,
Wang MeiXiang
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201200459
Subject(s) - enantioselective synthesis , intramolecular force , enantiomer , aldehyde , nucleophile , chemistry , nucleophilic addition , catalysis , stereochemistry , combinatorial chemistry , organic chemistry
Stable tertiary enamides and enecarbamates undergo highly enantioselective intramolecular nucleophilic addition to aldehyde units catalyzed by chiral binol–Ti complexes under mild conditions to produce the title compounds in up to 99.5 % or greater enantiomeric excess. A positive nonlinear effect was detected and the formation of binol–Ti aggregates suggests an intricate asymmetric catalytic pathway.