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Stereospecific and Stereoselective Preparation of 2‐(1‐Hydroxyalkyl)‐1‐alkylcyclopropanols from α,β‐Epoxy Ketones and Bis(iodozincio)methane
Author(s) -
Nomura Kenichi,
Oshima Koichiro,
Matsubara Seijiro
Publication year - 2005
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.200501644
Subject(s) - stereospecificity , epoxide , intramolecular force , chemistry , epoxy , stereoselectivity , reagent , zinc , methane , ring (chemistry) , medicinal chemistry , ketone , stereochemistry , organic chemistry , catalysis
A coordinated attack : The reaction of α,β‐epoxy ketones with bis(iodozincio)methane produces 2‐(1‐hydroxyalkyl)‐1‐alkylcyclopropanols diastereoselectively (see scheme). The reaction proceeds by the coordination and diastereoselective addition of the zinc reagent to the carbonyl group followed by a stereospecific intramolecular attack on the epoxide ring.