STUDIES ON STEREOSELECTIVE ELECTROPHILIC CYANATION

Authors
BUTTKE K NICLAS HJ
Citation
K. Buttke et Hj. Niclas, STUDIES ON STEREOSELECTIVE ELECTROPHILIC CYANATION, Journal fur praktische Chemie, Chemiker-Zeitung, 340(7), 1998, pp. 669-675
Citations number
40
Categorie Soggetti
Chemistry,"Chemistry Applied
Journal title
Journal fur praktische Chemie, Chemiker-Zeitung → ACNP
ISSN journal
09411216
Volume
340
Issue
7
Year of publication
1998
Pages
669 - 675
Database
ISI
SICI code
0941-1216(1998)340:7<669:SOSEC>2.0.ZU;2-U
Abstract
The enantioselective, electrophilic cyanation of the enolates of 2-sub stituted 1-tetralones 3 is described. Enantiomerically pure 2-cyanato- 1,1'-binaphthyl derivatives 2, 6a and b are used as cyanating agents. The influence of solvent, temperature, additives and the method of eno late formation are investigated. Best results are obtained with 48% ee in the case of compound 2 and 60% ee in the case of compound 6b if th e enolate is prepared from the corresponding silyl enol ether 7 and To luene is used as solvent.