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Title: Direct Amine-Catalyzed Enantioselective Synthesis of Pentacyclic Dibenzo[b,f][1,4]oxazepine/Thiazepine-Fused Isoquinuclidines along with DFT Calculations
Authors: Kumar, Dalip
Kumar, Indresh
Keywords: Chemistry
Purification
Stereoselectivity
Fossil fuels
Issue Date: 8-Oct-2020
Publisher: ACS
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.
URI: https://pubs.acs.org/doi/10.1021/acs.joc.0c02141
http://dspace.bits-pilani.ac.in:8080/xmlui/handle/123456789/3015
Appears in Collections:Department of Chemistry

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