Herstellung und Umsetzungen von ( R,R )‐ und ( S,S )‐3‐Trifluormethyloxiran‐2‐carbonsäure‐ethylester, einem vielseitigen, leicht zugänglichen CF 3 ‐haltigen Synthesebaustein | Zendy

BusscheHünnefeld Christoph Von Dem | Zendy; Seebach Dieter | Zendy

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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.

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