Enantioselective [4 + 2] cycloaddition of cyclic N-sulfimines and acyclic enones or ynones: a concise route to sulfamidate-fused 2,6-disubstituted piperidin-4-ones.
A concise route to valuable sulfamate-fused 2,6-disubstituted piperidin-4-ones or 2,3-dihydropyridin-4(1H)-ones in good yield with high diastereo- and enantioselectivity is presented. The combination of chiral primary amine and o-fluorobenzoic acid efficiently promoted an asymmetric [4 + 2] cycloaddition reaction of N-sulfonylimines and enones or ynones. The cycloaddition reaction between cyclic N-sulfonylimines and ynones is first reported.
Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry & Chemical Engineering, China West Normal University , Nanchong 637009, China , and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, China.
Yong
Y
Liu
Tai-Ran
TR
Kang
Quan-Zhong
QZ
Liu
Lian-Mei
LM
Chen
Ya-Chuan
YC
Wang
Jie
J
Liu
Yong-Mei
YM
Xie
Jin-Liang
JL
Yang
Long
L
He
D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D061565:Cycloaddition Reaction; D007097:Imines / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D010881:Piperidones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry
D000588:Amines; D007097:Imines; D007659:Ketones; D010881:Piperidones; D013450:Sulfones