Sequential coupling of zincated hydrazone, alkenylboronate, and electrophile that creates several contiguous stereogenic centers.
A zincated N,N-dimethylhydrazone of a ketone undergoes stereospecific syn addition to E- or Z-alkenylboronate to generate a gamma-Zn/B dimetallic intermediate, which reacts with a carbon electrophile to give a gamma-borylhydrazone in good yield with excellent diastereoselectivity, creating two to four contiguous stereogenic centers in a one-pot reaction.
Nakamura
Masaharu
M
Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. masaharu@chem.s.u-tokyo.ac.jp
Hatakeyama
Takuji
T
Hara
Kenji
K
Fukudome
Hiroki
H
Nakamura
Eiichi
E