SYNTHESIS OF HOMOCHIRAL L-(S)-TERT-LEUCINE VIA A LIPASE-CATALYZED DYNAMIC RESOLUTION PROCESS

Authors
TURNER NJ WINTERMAN JR MCCAGUE R PARRATT JS TAYLOR SJC
Citation
Nj. Turner et al., SYNTHESIS OF HOMOCHIRAL L-(S)-TERT-LEUCINE VIA A LIPASE-CATALYZED DYNAMIC RESOLUTION PROCESS, Tetrahedron letters, 36(7), 1995, pp. 1113-1116
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
7
Year of publication
1995
Pages
1113 - 1116
Database
ISI
SICI code
0040-4039(1995)36:7<1113:SOHLVA>2.0.ZU;2-D
Abstract
Treatment of (+/-)-2-phenyl-4-tert-butyloxazolin-5(4H)-8 with Lipozyme (R) (Mucor miehei) in toluene containing n-butanol and a catalytic amo unt of triethylamine resulted in a 94% yield of (S)-N-benzoyl tert-leu cine butyl ester 9 (99.5% e.e.). Subsequent two step hydrolysis (Alcal ase(R) followed by 6N HCl, reflux) yielded homochiral L-(S)-tert-leuci ne 1.