Stereocontrol in the reduction of meso-imides using oxazaborolidine, leading to a facile synthesis of (+)-deoxybiotin

Authors
Shimizu, M Nishigaki, Y Wakabayashi, A
Citation
M. Shimizu et al., Stereocontrol in the reduction of meso-imides using oxazaborolidine, leading to a facile synthesis of (+)-deoxybiotin, TETRAHEDR L, 40(50), 1999, pp. 8873-8876
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
50
Year of publication
1999
Pages
8873 - 8876
Database
ISI
SICI code
0040-4039(199912)40:50<8873:SITROM>2.0.ZU;2-A
Abstract
Highly enantioselective reduction of meso-imides was conducted using oxazab orolidine derived from L-threonine and borane-THF complex to give lactams i n high enantiomeric purity. This methodology was successfully applied to th e synthesis of (+)-deoxybiotin in an enantio-controlled manner in good over all yield. (C) 1999 Elsevier Science Ltd. All rights reserved.