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Enantio‐ and Diastereoselective Iodocyclopropanation of Allylic Alcohols by Using a Substituted Zinc Carbenoid
Author(s) -
Beaulieu LouisPhilippe B.,
Zimmer Lucie E.,
Charette André B.
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200902228
Subject(s) - allylic rearrangement , carbenoid , enantioselective synthesis , zinc , chemistry , combinatorial chemistry , stoichiometry , ligand (biochemistry) , computer science , organic chemistry , catalysis , rhodium , biochemistry , receptor
(Zinc)redible! 2,3‐Disubstituted and 2,3‐trisubstituted iodocyclopropanes can be accessed in enantiomerically enriched form by using the enantioselective Simmons–Smith iodocyclopropanation of allylic alcohols in the presence of the stoichiometric dioxaborolane chiral ligand. These iodocyclopropanes serve as versatile chiral building blocks towards highly functionalized 1,2,3‐trisubstituted cyclopropanes (see scheme).