ISSN:
0009-2940
Keywords:
Glycidic esters
;
Oxiranecarboxylic esters
;
Threonine
;
allo-Threonine
;
Epoxy alcohols
;
Flustrates
;
Payne rearrangement
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Preparation and Reactions of Ethyl (R,R)- and (S,S)-3-Trifluoromethyloxirane-2-carboxylate, a Versatile, Easily Accessible CF3-Containing Building Block for SynthesisA facile three-step route has been elaborated leading from 4,4,4-trifluoro-3-oxobutanoate to the trifluoro glycidic ester 1 mentioned in the title (0.1-mole scale). Reactions with azide (→ 4, 5) and with organometallic compounds such as cuprates (→ 3, 6), lithium (→ 7, 8), and magnesium derivatives (→ 9-11) furnish novel enantiomerically pure trifluoromethyl-substituted carboxylic esters, ketones, diols, and epoxy alcohols. The latter ones undergo selective isomerizations by Payne rearrangement (11 → 12) in aqueous NaOH/acetone or tert-butyl alcohol.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19921250538
