Dual catalytic enantioselective desymmetrization of allene-tethered cyclohexanones

Dual catalytic enantioselective desymmetrization of allene-tethered cyclohexanones

The construction of enantioenriched azabicyclo[3.3.1]nonan-6-one heterocycles via an enantioselective desymmetrization of allene-linked cyclohexanones, enabled through a dual catalytic system, that provides synchronous activation of the cyclohexanone with a chiral prolinamide and the allene with a c...

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Մատենագիտական մանրամասներ
Հիմնական հեղինակներ: Zhang, L, Yamazaki, K, Leitch, JA, Manzano, R, Atkinson, AM, Hamlin, TA, Dixon, DJ
Ձևաչափ: Journal article
Լեզու:English
Հրապարակվել է: Royal Society of Chemistry 2020
Նկարագրություն
Ամփոփում:The construction of enantioenriched azabicyclo[3.3.1]nonan-6-one heterocycles via an enantioselective desymmetrization of allene-linked cyclohexanones, enabled through a dual catalytic system, that provides synchronous activation of the cyclohexanone with a chiral prolinamide and the allene with a copper(I) co-catalyst to deliver the stereodefined bicyclic core, is described. Successful application to oxygen analogues was also achieved, thereby providing a new enantioselective synthetic entry to architecturally complex bicyclic ethereal frameworks. The mechanistic pathway and the origin of enantio- and diastereoselectivities has been uncovered using density functional theory (DFT) calculations.

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