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The Impact of the Mukaiyama Aldol Reaction in Total Synthesis
Author(s) -
Kan S. B. Jennifer,
Ng Kenneth K.H.,
Paterson Ian
Publication year - 2013
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.201303914
Subject(s) - aldol reaction , carbon skeleton , total synthesis , chemistry , construct (python library) , natural product , boron , carbon fibers , natural (archaeology) , stereochemistry , computer science , organic chemistry , biology , catalysis , algorithm , programming language , paleontology , composite number
Abstract Four decades since Mukaiyama’s first reports on the successful application of silicon and boron enolates in directed aldol reactions, the ability of this highly controlled carbon–carbon bond‐forming method to simultaneously define stereochemistry, introduce complexity, and construct the carbon skeleton with a characteristic 1,3‐oxygenation pattern has made it a powerful tool for natural product synthesis. This Minireview highlights a number of representative total syntheses that demonstrate the impact of the Mukaiyama aldol reaction and discusses the underlying mechanistic rationale that determines the stereochemical outcomes.