Citation
F. Yuste et al., Synthesis of enantiomerically pure 2-amino alcohols from amino acids mediated by sulfoxides, TETRAHEDR-A, 11(15), 2000, pp. 3079-3090
Citations number
67
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166
→ ACNP
Volume
11
Issue
15
Year of publication
2000
Pages
3079 - 3090
Database
ISI
SICI code
0957-4166(20000811)11:15<3079:SOEP2A>2.0.ZU;2-X
Abstract
Enantiomerically pure (R-1,S-2)- and (S-1,S-2)-2-amino alcohols can be easi
ly synthesized by stereodivergent reduction of alpha'-(N-Boc)amino beta-ket
o sulfoxides (easily synthesized from readily available N-Boc amino eater h
ydrochlorides) with DIBAH (clr 82-92%) and DIBAH/ZnBr2 (de 80%), followed b
y hydrogenolysis of the C-S bond of the resulting hydroxy sulfoxides and fi
nal hydrolysis of the N-Boc protecting group. (C) 2000 Elsevier Science Ltd
. All rights reserved.