The reaction of enamines with epoxides

Britten, A. Z.; Owen, W. S.; Went, Charles

doi:10.1016/s0040-4020(01)82848-9

Cited by 16 publications

(2 citation statements)

References 8 publications

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“…Moreover, compounds 4a-l can be regarded as masked 1,5-diketones, the deketalization of which would generate the corresponding open 1,4-addition adducts. 27 In future work, we plan to expand the scope of this protocol to include noncyclic MBH adducts 31 and a variety of enamines using various catalysts. 20,[32][33][34]…”

Section: Syn Lettmentioning

confidence: 99%

“…We believe that the mechanism of this reaction involves the initial conjugate addition of enamine 2a to the ZnBr 2activated MBH adduct 3a to afford the corresponding iminium intermediate I, followed by intramolecular addition 25,26 of the zinc alkoxide function to the transiently formed iminium ion to give the N,O-ketal zinc enolate II. Final hydrolytic quench affords the N,O-ketal 4a 18,27 (Scheme 3, Table 2, entry 4). From a mechanistic viewpoint, it is worth noting that the role of ZnBr 2 in the present reaction is different from that of our previous study.…”

Section: Table 2 Optimization Of the Reaction Conditions For The Synthesis Of 4a Amentioning

confidence: 99%

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First Zinc Bromide Promoted Annulative Domino Reactions between Enamines and Cyclic Morita–Baylis–Hillman Alcohols: Synthesis of N,O-Ketals

Bouhalleb

Meddeb

Bourguiba

et al. 2020

Synlett

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A new efficient ZnBr2-mediated annulative domino reaction between enamines and cyclic Morita–Baylis–Hillman (MBH) alcohols is disclosed. The process involves a tandem sequence (intermolecular conjugate addition of enamines to MBH alcohols and intramolecular nucleophilic addition of the hydroxyl moiety to the transiently generated iminium ion), affording the corresponding N,O-ketals diastereoselectively in good yields.

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