Asymmetric Mukaiyama-Michael addition of acyclic enones catalyzed by allo-threonine-derived B-aryloxazaborolidinones.
[reaction: see text] O-(2-Naphthoyl)-N-tosyl-L-allo-threonine-derived B-phenyloxazaborolidinone catalyzes the asymmetric Mukaiyama-Michael addition of simple acyclic enones to give adducts of 54-85% ee. 2,6-Diisopropylphenol as an additive is demonstrated to effectively retard the undesirable Si(+)-catalyzed racemic pathway.
Harada
T
T
Department of Chemistry, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto, 606-8585, Japan. harada@chem.kit.ac.jp
Iwai
H
H
Takatsuki
H
H
Fujita
K
K
Kubo
M
M
Oku
A
A