Diastereoselective electrophilic fluorination of enantiopure alpha-silylketones using N-fluoro-benzosulfonimide: Regio- and enantioselective synthesis of alpha-fluoroketones

Authors
Enders, D Faure, S Potthoff, M Runsink, J
Citation
D. Enders et al., Diastereoselective electrophilic fluorination of enantiopure alpha-silylketones using N-fluoro-benzosulfonimide: Regio- and enantioselective synthesis of alpha-fluoroketones, SYNTHESIS-S, (15), 2001, pp. 2307-2319
Citations number
39
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
15
Year of publication
2001
Pages
2307 - 2319
Database
ISI
SICI code
0039-7881(200111):15<2307:DEFOEA>2.0.ZU;2-B
Abstract
alpha -Fluoroketones 6 are synthesized in good yields and high enantiomeric excesses (ee = 87- greater than or equal to 96%) from the corresponding si mple cyclic and acyclic ketone precursors. The procedure involves a regio- and diastereoselective electrophilic fluorination of enantiopure alpha -sil ylketones 2 (de = 37- greater than or equal to 98%) using commercially avai lable N-fluorobenzosulfonimide as fluorinating agent, followed by a racemiz ation-free cleavage of the silyl directing group with almost quantitative y ields.