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Bifunctional squaramide catalyzed stereoselective Mannich reaction of α-azido ketones with isatin-derived ketimines

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Abstract

Asymmetric organocatalytic Mannich reaction of α-azido ketones and N-Boc protected isatin-derived ketimines were investigated for the first time. Examination of both 2-adamantyl and 3,5-bis(trifluoromethyl)aniline substituted quinine-based squaramides afforded chiral Mannich bases with two contiguous stereogenic centers in high yields (up to 97%) and stereoselectivity (up to dr = 24 : 1 syn : anti and 96% ee). Azido and masked amino functionalities of the potent heterocycle precursor adducts were utilized in representative examples.

Graphical abstract: Bifunctional squaramide catalyzed stereoselective Mannich reaction of α-azido ketones with isatin-derived ketimines

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Article information


Submitted
11 Oct 2019
Accepted
11 Dec 2019
First published
11 Dec 2019

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Bifunctional squaramide catalyzed stereoselective Mannich reaction of α-azido ketones with isatin-derived ketimines

S. Karahan and C. Tanyeli, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02208B

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