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Issue 5, 1977
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Asymmetric synthesis. Part 5. Asymmetric reduction of phenyl trifluoromethyl ketone with chiral alkoxy-aluminium and -magnesium halides

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.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1977, 576-578
Article type
Paper

Asymmetric synthesis. Part 5. Asymmetric reduction of phenyl trifluoromethyl ketone with chiral alkoxy-aluminium and -magnesium halides

D. Nasipuri and P. K. Bhattacharya, J. Chem. Soc., Perkin Trans. 1, 1977, 576
DOI: 10.1039/P19770000576

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