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Subtle Variations in the Long‐Range Transmission of Stereochemical Information: Matched and Mismatched Aldol Reactions
Author(s) -
Wu Zhicai,
Zhang Fei,
Danishefsky Samuel J.
Publication year - 2000
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 - 10.1002/1521-3773(20001215)39:24<4505::aid-anie4505>3.0.co;2-2
Subject(s) - stereocenter , aldol reaction , aldol condensation , covalent bond , chemistry , focus (optics) , stereochemistry , enantioselective synthesis , organic chemistry , catalysis , physics , optics
Remote influences : The diastereofacial sense in which covalent bond formation is affected by remote stereogenic loci has been studied. An intermediate in the synthesis of the epothilones was the focus of these studies. Condensation of 1 and 2 gives rise to the single product in a “matched” aldol reaction. The transition states of the various reactions are discussed.