An inverse electron-demand diene-transmissive hetero-Diels-Alder reaction of N-sulfonyl-[3]-1-azadendralenes for stereocontrolled synthesis of polyhydroquinolines

作者：Kanai Kan; Kobayashi Satoru; Kudo Kenji; Honjo Takuya; Otani Takashi^*; Saito Takao

来源：Tetrahedron Letters, 2015, 56(36): 5090-5093.

DOI：10.1016/j.tetlet.2015.07.040

• Diene-transmissive Diels-Alder reaction
• Hetero-Diels-Alder reaction
• Inverse electron-demand Diels-Alder reaction
• Polyhydroquinoline
• Stereoselective reaction

Cross-conjugated 1-azatrienes ([3]-1-azadendralenes) bearing a sulfonyl group on the nitrogen atom were converted to various polyhydroquinolines with multiple stereocentres via a diene-transmissive hetero-Diels-Alder (DA) reaction consisting of an inverse electron-demand aza-DA reaction with electron-rich dienophiles followed by a stereoselective DA reaction with electron-deficient dienophiles.

• 出版日期2015-9-2