Optically Active Axially Chiral Anilide and Maleimide Derivatives as New Chiral Reagents: Synthesis and Application to Asymmetric Diels-Alder Reaction.
New axially chiral N-acryl-N-allyl-o-tert-butylanilide and N-(o-tert-butylphenyl)-2-methylmaleimide with high optical purity and definite absolute configurations were prepared from o-tert-butylaniline and (S)-O-acetyl lactic acid or (R)-2-methylsuccinic acid, respectively. Iodine- or Lewis acid-mediated asymmetric Diels-Alder reaction of these axially chiral compounds with various dienes proceeded with high endo and diastereofacial selectivity.
Kitagawa
Osamu
O
Rigaku Corporation, 3-9-12 Matsubara-cho, Akishima, Tokyo 196, Japan.
Izawa
Hirotaka
H
Sato
Kiyonobu
K
Dobashi
Akira
A
Taguchi
Takeo
T
Shiro
Motoo
M