This article is cited in 1 paper

Communications

Organocatalytic domino formation of (3R,3aS,9bR)-configured 3-aryl-3a-benzamido-1,3a,4,9b-tetrahydrochromeno[4,3-b]pyrroles in carbon dioxide medium

O. V. Turova, A. G. Nigmatov, E. V. Filatova, A. A. Vasil'ev, S. G. Zlotin

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: Asymmetric cycloaddition/intramolecular rearrangement domino reaction of 2-(2-hydroxybenzylideneamino)- malonates with 4-arylidene-2-phenyloxazol-5(4H)-ones can be efficiently carried out in sub- or supercritical carbon dioxide to afford (3R,3aS,9bR)-3-aryl-3a-benzamido-4-oxo-1,3a,4,9b-tetrahydrochromeno[4,3-b]pyrrole-2,2(3H)- dicarboxylates in high yields with up to 99% ee. Excellent stereoinduction is provided in this process by the use of bifunctional hybrid organocatalyst consisting of squaramide (thiourea) and chiral tertiary amine units.

Keywords: organocatalysis, domino reactions, squaramides, 1,3a,4,9b-tetrahydrochromeno[4,3-b]pyrroles, liquid carbon dioxide, 2-(2-hydroxybenzylideneamino)malonates, 4-arylidene-2-phenyloxazol-5(4H)-ones.

Language: English

DOI: 10.1016/j.mencom.2024.09.022

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