Asymmetric organocatalytic Michael addition/aza-cyclization coupled with sequential Michael addition for synthesizing densely polycyclic-fused dihydroquinolines

作者：Yu Mirim; Kim Sung Gon^*

来源：Tetrahedron Letters, 2015, 56(28): 4159-4162.

DOI：10.1016/j.tetlet.2015.04.112

• Organocatalysis
• Asymmetric catalysis
• Domino reaction
• Aza-cyclization
• 1,4-Dihydroquinoline

A highly efficient sequential process based on organocatalysis for the asymmetric synthesis of polycyclicfused dihydroquinolines is described. In this synthesis, an asymmetric organocatalytic Michael/aza-cyclization domino reaction of 5-formylpent-2-enyl esters with N-protected-2-amino-beta-nitrostyrenes, followed by dehydration, affords the corresponding alpha,beta-unsaturated ester containing 1,4-dihydroquinoline products with high enantioselectivities (up to 99% ee). Subsequent organocatalytic intramolecular Michael reaction of the alpha,beta-unsaturated ester containing 1,4-dihydroquinoline adducts results in the formation of chiral tricyclic-fused dihydroquinolines.

• 出版日期2015-7-8