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Title: Enantio- and Diastereoselective Two-Pot Synthesis of Isoquinuclidines from Glutaraldehyde and N-Aryl Imines with DFT Calculations
Authors: Kumar, Indresh
Keywords: Chemistry
High-performance liquid chromatography
Solution chemistry
Stereoselectivity
Chemical reactions
Issue Date: 5-Sep-2019
Publisher: ACS
Abstract: A pot-economic method for the enantio- and diastereoselective synthesis of a [2.2.2] azabicyclic isoquinuclidine system is developed. This protocol involves the proline-catalyzed direct Mannich reaction-cyclization/IBX-mediated site-selective oxidation/NaBH4-reduction sequence between glutaraldehyde and imines to generate in situ chiral 1,2-DHPs, followed by the diastereoselective Diels–Alder reaction with N-aryl maleimides furnishing isoquinuclidines in overall five steps. A variety of isoquinuclidines having five-contiguous chiral centers, including an all-carbon quaternary, were prepared with high yields (up to 78%) and excellent stereoselectivity (>50:1 dr, and up to >99:1 er). DFT calculations support the observed high stereoselective reaction outcome.
URI: https://pubs.acs.org/doi/abs/10.1021/acs.joc.9b01865
http://dspace.bits-pilani.ac.in:8080/xmlui/handle/123456789/3160
Appears in Collections:Department of Chemistry

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