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Catalytic asymmetric cyclopropanation of allylic alcohols with titanium-TADDOLate: scope of the cyclopropanation reaction.

Authors :
Charette AB
Molinaro C
Brochu C
Source :
Journal of the American Chemical Society [J Am Chem Soc] 2001 Dec 12; Vol. 123 (49), pp. 12168-75.
Publication Year :
2001

Abstract

A substoichiometric amount of titanium-TADDOLate complex was effective at catalyzing the cyclopropanation reaction of allylic alcohols in the presence 1 equiv of bis(iodomethyl)zinc. After initial optimization of the catalyst structure, excellent yields and enantiomeric ratios were obtained for 3-aryl- or 3-heteroaryl-substituted allylic alcohols (up to 97:3). Alkyl-substituted allylic alcohols gave modest yields and enantiomeric ratios (up to 87:13) but these compare favorably with those observed with other substoichiometric chiral ligands. The full synthetic scope of the reaction is presented in this paper.

Details

Language :
English
ISSN :
0002-7863
Volume :
123
Issue :
49
Database :
MEDLINE
Journal :
Journal of the American Chemical Society
Publication Type :
Academic Journal
Accession number :
11734015
Full Text :
https://doi.org/10.1021/ja0108382