Catalytic Meerwein-Pondorf-Verley reduction by simple aluminum complexes

Citation
Ej. Campbell et al., Catalytic Meerwein-Pondorf-Verley reduction by simple aluminum complexes, ORG LETT, 3(15), 2001, pp. 2391-2393
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
15
Year of publication
2001
Pages
2391 - 2393
Database
ISI
SICI code
1523-7060(20010726)3:15<2391:CMRBSA>2.0.ZU;2-G
Abstract
[GRAPHICS] Catalytic MPV reduction was successfully carried out using simple aluminum precatalysts, Alkylaluminum reagents were converted to a low-aggregation al uminum alkoxide that was highly active for the MPV reduction of several car bonyl substrates in high yield (50-99%) using (PrOH)-Pr-i as the reducing a gent. A high degree of cis/trans selectivity was achieved in the reduction of 2-methylcyclohexanone (cis/trans = 20/80) by (PrOH)-Pr-i. When chiral hy dride sources were utilized in the reduction of 2 chloroacetophenone, high enantioselectivity (68-80% ee) was observed.