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Stereoselective Pinacol‐Type Rearrangement of 2,3‐Epoxy Alcohols with Retention of Configuration Mediated by Bis(iodozincio)methane
Author(s) -
Matsubara Seijiro,
Yamamoto Hiromasa,
Oshima Koichiro
Publication year - 2002
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(20020802)41:15<2837::aid-anie2837>3.0.co;2-x
Subject(s) - walden inversion , stereoselectivity , epoxy , pinacol , methane , chemistry , stereochemistry , organic chemistry , catalysis
Retention of the configuration is observed in the pinacol‐type rearrangement of 2,3‐epoxy alcohols 1 in the presence of bis(iodozincio)methane ( 2 ). The 1,3‐migration of the hydroxymethyl group affords an intermediate 2‐hydroxyaldehyde, which is methylenated by 2 in situ to give homoallyl alcohol 3 .