Regioselective allylzincation of alkenylboronate.
[reaction: see text] Boryl substitution on an olefin activates the olefinic double bond toward addition of an organozinc reagent. Addition of an allylic zinc reagent to an alkenylboronate thus takes place smoothly to afford a variety of gem-zincio/boryl species. Theoretical studies with density functional calculations on the reaction pathway revealed that the reaction proceeds via a zincio-ene reaction rather than a bora-Claisen rearrangement.
Nakamura
M
M
Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. nakamura@chem.s.u-tokyo.ac.jp
Hara
K
K
Hatakeyama
T
T
Nakamura
E
E