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N-Heterocyclic Carbene-Catalyzed Atroposelective Synthesis of N-N Axially Chiral 3-Amino Quinazolinones

Balanna, K and Barik, S and Barik, S and Shee, S and Manoj, N and Gonnade, RG and Biju, AT (2023) N-Heterocyclic Carbene-Catalyzed Atroposelective Synthesis of N-N Axially Chiral 3-Amino Quinazolinones. In: ACS Catalysis, 13 (13). pp. 8752-8759.

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Official URL: https://doi.org/10.1021/acscatal.3c01709


Although the atroposelective synthesis of biaryls and related compounds bearing axially chiral C-C bonds is well-known, the synthesis of axially chiral C-N bond-containing compounds is relatively less explored, and the construction of axially chiral N-N bonds has received only scant attention. Demonstrated herein is the N-heterocyclic carbene (NHC)-catalyzed selective amidation reaction, leading to the atroposelective synthesis of N-N axially chiral 3-amino quinazolinones. The NHC-catalyzed reaction of quinazolinones containing a free N-H moiety with α,β-unsaturated aldehydes under oxidative conditions furnished the atropisomeric quinazolinone derivatives under mild conditions and broad scope. Preliminary studies on experimental and density functional theory-based N-N rotational barrier determination are also presented.

Item Type: Journal Article
Publication: ACS Catalysis
Publisher: American Chemical Society
Additional Information: The copyright for this article belongs to the American Chemical Society.
Keywords: amino quinazolinones; asymmetric catalysis; axial chirality; N-heterocyclic carbenes; organocatalysis
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 01 Aug 2023 05:11
Last Modified: 01 Aug 2023 05:11
URI: https://eprints.iisc.ac.in/id/eprint/82728

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