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

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 Full article

Journal

Mendeleev Communications
ISSN: 1364-551X , E-ISSN: 0959-9436

Output data

Year: 2024, Volume: 34, Number: 5, Pages: 694-697 Pages count : 4 DOI: 10.1016/j.mencom.2024.09.022

Tags

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

Authors

Turova Olga V. ¹ , Nigmatov Albert G. ¹ , Filatova Evgeniya V. ¹ , Vasil’ev Andrei A. ¹ , Zlotin Sergei G. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation

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.

Turova O.V. , Nigmatov A.G. , Filatova E.V. , Vasil’ev A.A. , Zlotin S.G.
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
Mendeleev Communications. 2024. V.34. N5. P.694-697. DOI: 10.1016/j.mencom.2024.09.022 WOS Scopus OpenAlex

Submitted:	May 23, 2024
Published online:	Oct 14, 2024

≡ Web of science:	WOS:001336187600001
≡ Scopus:	2-s2.0-85206178382
≡ OpenAlex:	W4403388800