Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Origins of Stereoselectivity of Enamine–Iminium-Activated Nazarov Cyclizations by Vicinal Diamines

Origins of Stereoselectivity of Enamine–Iminium-Activated Nazarov Cyclizations by Vicinal Diamines
Yu-hong Lam, Adam Simon, K. N. Houk
The mechanism and sources of asymmetric induction in Nazarov reactions reported by Tius and co-workers have been determined with quantum chemical calculations. A chiral vicinal diamine forms an enamine–iminium adduct with α-ketoenones, and this undergoes a cationic conrotatory electrocyclization. The chiral diamine imparts stereocontrol in the enamine–iminium complex by forming a six-membered ring that favors one helicity of the electrocyclization transition state.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01606

DOI: 10.1021/acs.joc.7b01606

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