Regioselective allylzincation of alkenylboronate

Citation
M. Nakamura et al., Regioselective allylzincation of alkenylboronate, ORG LETT, 3(20), 2001, pp. 3137-3140
Citations number
25
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
1523-7060 → ACNP
Volume
3
Issue
20
Year of publication
2001
Pages
3137 - 3140
Database
ISI
SICI code
1523-7060(20011004)3:20<3137:RAOA>2.0.ZU;2-R
Abstract
[GRAPHICS] Boryl substitution on an olefin activates the olefinic double bond toward a ddition of an organozinc reagent. Addition of an allylic zinc reagent to an alkenylboronate thus takes place smoothly to afford a variety of gem-zinci o/boryl species. Theoretical studies with density functional calculations o n the reaction pathway revealed that the reaction proceeds via a zincio-ene reaction rather than a bora-Claisen rearrangement.