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

Highly enantioselective reduction of meso-imides was conducted using oxazaborolidine derived from l-threonine and borane-THF complex to give lactams in high enantiomeric purity. This methodology was successfully applied to the synthesis of (+)-deoxybiotin in an enantio-controlled manner in good over...

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Bibliographic Details
Published in:Tetrahedron letters 1999-12, Vol.40 (50), p.8873-8876
Main Authors: Shimizu, Makoto, Nishigaki, Yoshimasa, Wakabayashi, Akinobu
Format: Article
Language:English
Subjects:
(+)-deoxybiotin
l-threonine
meso-imide
oxazaborolidine
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Summary:Highly enantioselective reduction of meso-imides was conducted using oxazaborolidine derived from l-threonine and borane-THF complex to give lactams in high enantiomeric purity. This methodology was successfully applied to the synthesis of (+)-deoxybiotin in an enantio-controlled manner in good overall yield. Enantioselective reduction of meso-imides was conducted using oxazaborolidine derived from L-threonine and borane-THF complex to give lactams in high enantiomeric purity. This methodology was applied to the synthesis of (+)-deoxybiotin.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)01864-X