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Issue 3, 2020
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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., 2020,18, 479-487
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, 18, 479
DOI: 10.1039/C9OB02208B

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