Asymmetric synthesis. Part 5. Asymmetric reduction of phenyl trifluoromethyl ketone with chiral alkoxy-aluminium and -magnesium halides
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 576-578
- https://doi.org/10.1039/p19770000576
Abstract
Phenyl trifluoromethyl ketone has been asymmetrically reduced with a number of chiral alkoxy-aluminium and -magnesium halides derived from bornan-2-exo- and -endo-ols, p-menthan-3-ol, and 1-phenylethanol. Bornan-2-endo-yloxyaluminium dichloride and p-menthan-3-yloxyaluminium dichloride are highly stereoselective and reduce the ketone to give 2,2,2-trifluoro-1 -phenylethanol with 68 and 77% enantiomeric excess, respectively. The results are discussed in terms of appropriate transition states.Keywords
This publication has 0 references indexed in Scilit: