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Stereoselective Ring Expansion of Vinyl Oxiranes: Mechanistic Insights and Natural Product Total Synthesis
Author(s) -
Brichacek Matthew,
Batory Lindsay A.,
Njardarson Jon T.
Publication year - 2010
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.200906830
Subject(s) - stereoselectivity , chemistry , ring (chemistry) , natural product , catalysis , total synthesis , stereochemistry , organic chemistry , combinatorial chemistry , computational chemistry
What a (strain) relief! The first broadly applicable, catalytic, and stereoselective vinyl oxirane ring expansion is described (see scheme; hfacac=hexafluoroacetylacetonate). The stereoselectivity was influenced by several reaction parameters, and kinetic studies support a mechanistic proposal involving the in situ formation of a more reactive catalytic species. This ring‐expansion reaction has been employed in the asymmetric total synthesis of (+)‐goniothalesdiol.