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Direct Amine-Catalyzed Enantioselective Synthesis of Pentacyclic Dibenzo[b,f][1,4]oxazepine/Thiazepine-Fused Isoquinuclidines along with DFT Calculations

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dc.contributor.author Kumar, Indresh
dc.contributor.author Kumar, Dalip
dc.date.accessioned 2021-10-27T04:27:09Z
dc.date.available 2021-10-27T04:27:09Z
dc.date.issued 2020
dc.identifier.uri https://pubs.acs.org/doi/10.1021/acs.joc.0c02141
dc.identifier.uri http://dspace.bits-pilani.ac.in:8080/xmlui/handle/123456789/3157
dc.description.abstract A direct protocol for the asymmetric synthesis of dibenzoxazepine/thiazepine-fused [2.2.2] isoquinuclidines is developed. The reaction proceeds through a proline-catalyzed direct Mannich reaction followed by an intramolecular aza-Michael cascade sequence between 2-cyclohexene-1-one and various tricyclic imines, like dibenzoxazepines/thiazepines, as an overall [4 + 2] aza-Diels–Alder reaction. A series of pentacyclic isoquinuclidines have been prepared, with complete endo-selectivity, in good to high yields and excellent enantioselectivity (>99:1). Density functional theory (DFT) calculations further support the observed high stereochemical outcome of the reaction. en_US
dc.language.iso en en_US
dc.publisher ACS en_US
dc.subject Chemistry en_US
dc.subject Purification en_US
dc.subject Stereoselectivity en_US
dc.subject Fossil fuels en_US
dc.title Direct Amine-Catalyzed Enantioselective Synthesis of Pentacyclic Dibenzo[b,f][1,4]oxazepine/Thiazepine-Fused Isoquinuclidines along with DFT Calculations en_US
dc.type Article en_US


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