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Trifluoromethyl group induced highly stereoselective synthesis of α-hydroxy carbonyl compounds

✍ Scribed by Yoshitomi Morizawa; Arata Yasuda; Keiichi Uchida

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
208 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

The reaction of enolate prepared from ethyl 3-methyl-4,4,4-trifluorobutyrate with Mo05-Py-HMPA complex provides ethyl (2S*,3S*)-2-hydroxy-3methyl-4,4,4_trifluorobutyrate predominantly. In contrast, NaBH4 reduction of the corresponding 2-oxobutyrate affords (2R* ,3S*)-hydroxyester preferentially.

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The dwzt oxldatron of enolates with &methylchoxirane ( as a solunon m acetone ) provides the ahydroxy &nvanves m excellent yield The converSlon of enohzable ketones to their correspondmg a-hydroxy denvatlves 1s an important synthenc transformanon and has received a great deal of attennon la2 The cl