Diastereoselective hydroboration of chiral enamines using an enantiomerically pure amine from an industrial waste material as the source of chirality

Authors
Pennemann, H Wallbaum, S Martens, J
Citation
H. Pennemann et al., Diastereoselective hydroboration of chiral enamines using an enantiomerically pure amine from an industrial waste material as the source of chirality, TETRAHEDR-A, 11(10), 2000, pp. 2133-2142
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
10
Year of publication
2000
Pages
2133 - 2142
Database
ISI
SICI code
0957-4166(20000602)11:10<2133:DHOCEU>2.0.ZU;2-S
Abstract
By a hydroboration/oxidation procedure ti ans-aminoalcohols with dr values from 74:26 to greater than or equal to 95:5 were obtained. A bicyclic amine derived from the unnatural amino acid 2-azabicyclic[3.3.0]octane-3-carboxy lic acid was used as the chiral precursor. The absolute configuration was c larified by X-ray structure of a descendant of the tr ans-aminoalcohols. (C ) 2000 Elsevier Science Ltd. All rights reserved.