Shee, S and Barik, S and Ghosh, A and Biju, AT (2021) Synthesis of Functionalized Dihydrocoumarins by NHC-Catalyzed 3 + 3 Annulation of Enals with 2-Substituted Naphthoquinones. In: Organic Letters, 23 (20). 8039 -8044.
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Abstract
The 3 + 3 annulation of α,β-unsaturated aldehydes with 2-substituted 1,4-naphthoquinones allowing the facile synthesis of functionalized dihydrocoumarins catalyzed by N-heterocyclic carbene (NHC) is reported. The initially formed NHC-homoenolates underwent an efficient Michael-isomerization-lactonization cascade to furnish the products. Preliminary studies on mechanism shed light on the homoenolate pathway over the intermediacy of the α,β-unsaturated acylazolium intermediates. Moreover, using chiral NHCs, the desired products were formed in up to 49% yield and 99:1 er. ©
Item Type: | Journal Article |
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Publication: | Organic Letters |
Publisher: | American Chemical Society |
Additional Information: | The copyright for this article belongs to American Chemical Society |
Department/Centre: | Division of Chemical Sciences > Organic Chemistry |
Date Deposited: | 26 Nov 2021 10:49 |
Last Modified: | 26 Nov 2021 10:49 |
URI: | http://eprints.iisc.ac.in/id/eprint/70465 |
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