Enantio- and diastereoselective hetero-Diels-Alder reactions between 2-aza-3-silyloxy-1,3-butadienes and aldehydes catalyzed by chiral dirhodium(II) carboxamidates.
The first catalytic asymmetric hetero-Diels-Alder reaction between 2-aza-3-silyloxy-1,3-butadienes and aldehydes is described. With dirhodium(II) tetrakis[N-benzene-fused-phthaloyl-(S)-piperidinonate], Rh(2)(S-BPTPI)(4), the cycloaddition reaction proceeded exclusively in an endo mode to give all-cis-substituted 1,3-oxazinan-4-ones in high yields with up to 98% ee.
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.
Yudai
Y
Watanabe
Takuya
T
Washio
Janagiraman
J
Krishnamurthi
Masahiro
M
Anada
Shunichi
S
Hashimoto
D000447:Aldehydes / Q000737:chemistry*; D002070:Butadienes / Q000737:chemistry*; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry*; D010078:Oxazines / Q000138:chemical synthesis / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D002070:Butadienes; D056831:Coordination Complexes; D010078:Oxazines; D012238:Rhodium