A chiral acrylate equivalent for metal-free Diels-Alder reactions: endo-2-acryloylisoborneol.
The principle of metal-free activation of enones toward the Diels-Alder reaction with dienes is demonstrated by exploiting the capability of Brønsted acids to activate alpha'-hydroxyenones through hydrogen bonding. The diastereoselective application of such a principle is nicely realized by using a newly designed family of camphor-based chiral enones, which upon catalytic action of either trifluoroacetic or triflic acid lead to the corresponding cycloadducts with high chemical and stereochemical efficiency.
Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain. qoppanic@sq.ehu.es
Claudio
C
Palomo
Mikel
M
Oiarbide
Jesús M
JM
García
Alberto
A
González
Ainara
A
Lecumberri
Anthony
A
Linden