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A novel method for the preparation of benzylidenecyclohexanes with high optical purity
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Mar2004, Vol. 45 Issue 11, p2399. 4p. - Publication Year :
- 2004
-
Abstract
- The enantioselective reaction of the α-thio carbanion derived from 1-phenyl-1-(phenylthio)-1-(tributylstannyl)methane with 4-substituted cyclohexanones in the presence of bis(oxazoline)s gave the products as a diastereomeric mixture. Each diastereomer obtained had high optical purity. The reaction of the α-seleno carbanion derived from the bis(phenylseleno)acetal also showed high enantioselectivity. The stereospecific elimination of the isolated diastereomers on treatment with methanesulfonyl chloride and triethylamine afforded axially chiral benzylidenecyclohexanes with high enantioselectivities up to 99% ee. [Copyright &y& Elsevier]
- Subjects :
- *CARBANIONS
*ALKENES
*CYCLOHEXANE
*ASYMMETRIC synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 45
- Issue :
- 11
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 12307438
- Full Text :
- https://doi.org/10.1016/j.tetlet.2004.01.099