1-Azadienes as regio- and chemoselective dienophiles in aminocatalytic asymmetric Diels-Alder reaction.
Electron-deficient 1-aza-1,3-butadienes containing a 1,2-benzoisothiazole-1,1-dioxide or 1,2,3-benzoxathiazine-2,2-dioxide motif act as regio- and chemoselective dienophiles in normal-electron-demand Diels-Alder reactions with HOMO-raised trienamines, rather than typical 4π-participation in inverse-electron-demand versions. The enantioenriched cycloadducts could be efficiently converted to spiro or fused frameworks with high structural and stereogenic complexity by a sequential aza-benzoin reaction or other transformations.
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu, Sichuan 610041, China, and College of Pharmacy, Third Military Medical University , Shapingba, Chongqing 400038, China.
Chao
C
Ma
Jing
J
Gu
Bin
B
Teng
Qing-Qing
QQ
Zhou
Rui
R
Li
Ying-Chun
YC
Chen
D000466:Alkadienes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000466:Alkadienes; D000588:Amines; D001372:Aza Compounds; D013141:Spiro Compounds