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