Catalytic enantioselective inverse electron demand hetero-Diels-Alder reaction with allylsilanes.
The first diastereo- and enantioselective inverse electron demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketoesters with allylsilanes is described. Chiral copper(II) catalysts successfully activate the β,γ-unsaturated α-ketoesters and promote the reaction with allylsilanes with excellent enantioselectivities. This process represents a new entry to chiral oxanes.
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603 (Japan) http://www.nubio.nagoya-u.ac.jp/nubio4/index.htm.
Yuki
Y
Matsumura
Takahiro
T
Suzuki
Akira
A
Sakakura
Kazuaki
K
Ishihara
Lewis acid; asymmetric catalysis; copper; cycloaddition; heterocycles