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Herstellung und Umsetzungen von ( R,R )‐ und ( S,S )‐3‐Trifluormethyloxiran‐2‐carbonsäure‐ethylester, einem vielseitigen, leicht zugänglichen CF 3 ‐haltigen Synthesebaustein
Author(s) -
BusscheHünnefeld Christoph Von Dem,
Seebach Dieter
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921250538
Subject(s) - chemistry , acetone , lithium (medication) , medicinal chemistry , bifunctional , alcohol , organic chemistry , polymer chemistry , catalysis , medicine , endocrinology
Preparation and Reactions of Ethyl ( R,R )‐ and ( S,S )‐3‐Trifluoromethyloxirane‐2‐carboxylate, a Versatile, Easily Accessible CF 3 ‐Containing Building Block for Synthesis A 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.