Organocatalytic enantioselective Diels-Alder reaction of dienes with alpha-(N,N-Diacylamino)acroleins.
Catalytic and highly enantioselective Diels-Alder reaction of cyclic and acyclic dienes with alpha-phthalimidoacroleins provides cyclic alpha-quaternary alpha-amino acid precursors. The conformationally flexible chiral ammonium salt of H-L-Phe-L-Leu-N(CH(2)CH(2)) 2-reduced triamine with pentafluorobenzensulfonic acid is very effective as an asymmetric catalyst for the Diels-Alder reaction.
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan. ishihara@cc.nagoya-u.ac.jp
Kazuaki
K
Ishihara
Kazuhiko
K
Nakano
Matsujiro
M
Akakura
D000171:Acrolein / Q000138:chemical synthesis* / Q000737:chemistry; D000215:Acylation; D000586:Amination; D002384:Catalysis; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D010797:Phthalimides / Q000737:chemistry; D013237:Stereoisomerism
D010797:Phthalimides; C037431:phthalimide; D000171:Acrolein