Asymmetric hydroboration of [E]- and [Z]-2-methoxy-2-butenes. Synthesis of(-)-[2R,3R]-butane-2,3-diol in > 97% ee

Authors
Murali, D Singaram, B Brown, HC
Citation
D. Murali et al., Asymmetric hydroboration of [E]- and [Z]-2-methoxy-2-butenes. Synthesis of(-)-[2R,3R]-butane-2,3-diol in > 97% ee, TETRAHEDR-A, 11(24), 2000, pp. 4831-4834
Citations number
14
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
24
Year of publication
2000
Pages
4831 - 4834
Database
ISI
SICI code
0957-4166(200012)11:24<4831:AHO[A[>2.0.ZU;2-6
Abstract
Asymmetric hydroboration of [E]- and [Z]-2-methoxy-2-butene, using (-)-diis opinocampheylborane at -25 degreesC in THF solvent, followed by oxidation u sing H2O2/NaOH, gave (-)-[2R,3R]- and (+)-[2R,3S]-3-methoxy-2-butanols in > 97 and 90% ee, respectively. (-)-[2R,3R]-3-Methoxy-2-butanol was converted to (-)-[2R,3R]-butane-2,3-diol (>97% ee, in an overall yield of 65%). (C) 2 001 Elsevier Science Ltd. All rights reserved.