1544337-00-9Relevant academic research and scientific papers
Exoselective 1,3-dipolar [3 + 6] cycloaddition of azomethine ylides with 2-acylcycloheptatrienes: Stereoselectivity and mechanistic insight
He, Zhao-Lin,Sheong, Fu Kit,Li, Qing-Hua,Lin, Zhenyang,Wang, Chun-Jiang
, p. 1365 - 1368 (2015/03/30)
A highly exo-selective 1,3-dipolar [3 + 6] cycloaddition of azomethine ylides with 2-acylcycloheptatrienes was realized with a Cu(I)/(S,Rp)-PPF-NHMe complex as the catalyst, leading to a diverse range of bridged piperidines with multiple functionalities in good yield with excellent stereoselectivity control. Theoretical calculations indicated a stepwise mechanism for this exo-selective [3 + 6] annulation, which accounts for the remarkable feature of this annulation: all of the larger substituent groups occupy the axial positions in the six-membered chairlike conformation of the piperidine ring.
Catalytic asymmetric 1,3-dipolar [3 + 6] cycloaddition of azomethine ylides with 2-Acyl cycloheptatrienes: Efficient construction of bridged heterocycles bearing piperidine moiety
Li, Qing-Hua,Wei, Liang,Wang, Chun-Jiang
supporting information, p. 8685 - 8692 (2014/07/07)
Conjugated cyclic trienes without nonbenzenoid aromatic characteristic were successfully employed as fine-tunable dipolarophiles in the Cu(I)-catalyzed asymmetric azomethine ylide-involved 1,3-dipolar [3 + 6] cycloaddition for the first time, affording a variety of bridged heterocycles bearing piperidine moiety in good yield with exclusive regioselectivity and excellent stereoselectivity. 2-Acyl group is the key factor that determines the annulation preferentially through [3 + 6]-pathway, while 2-ester group modulates the annulation through [3 + 2]-pathway.
