Enantiospecific and regioselective rhodium-catalyzed allylic alkylation: Diastereoselective approach to quaternary carbon stereogenic centers

Authors
Evans, PA Kennedy, LJ
Citation
Pa. Evans et Lj. Kennedy, Enantiospecific and regioselective rhodium-catalyzed allylic alkylation: Diastereoselective approach to quaternary carbon stereogenic centers, ORG LETT, 2(15), 2000, pp. 2213-2215
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
15
Year of publication
2000
Pages
2213 - 2215
Database
ISI
SICI code
1523-7060(20000727)2:15<2213:EARRAA>2.0.ZU;2-7
Abstract
[GRAPHICS] The enantiospecific and regioselective rhodium-catalyzed allylic alkylation of a series of chiral nonracemic allylic carbonates, followed by ozonolysi s and reductive lactonization, provides a convenient route to optically act ive gamma-lactones, Sequential alkylation and reductive alkylation furnishe d the alpha-quaternary-beta-ternary substituted gamma-lactone derivative as a greater than or equal to 10:1 mixture of diastereoisomers.