N-Fluorocinchonidinium tetrafluoroborate F-CD-BF4: purification and structure elucidation of this novel enantioselective electrophilic fluorinating agent

Authors
Cahard, D Audouard, C Plaquevent, JC Toupet, L Roques, N
Citation
D. Cahard et al., N-Fluorocinchonidinium tetrafluoroborate F-CD-BF4: purification and structure elucidation of this novel enantioselective electrophilic fluorinating agent, TETRAHEDR L, 42(10), 2001, pp. 1867-1869
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
10
Year of publication
2001
Pages
1867 - 1869
Database
ISI
SICI code
0040-4039(20010304)42:10<1867:NTFPAS>2.0.ZU;2-S
Abstract
The first ever enantiopure N-fluoro quaternary ammonium salt of cinchonidin e (F-CD-BF4) was prepared as an enantioselective fluorinating agent. A one- step transfer-fluorination of the quinuclidine moiety with Selectfluor(R) g ave the [N-F](+) reagent. The X-ray structure of F-CD-BF4 was determined, w hich shows the NF distance (1.409(7) Angstrom) close to that found in other N-F compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.