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Issue 28, 2018
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A chiral Brønsted acid-catalyzed highly enantioselective Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines

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Abstract

A chiral phosphoric acid-catalyzed asymmetric Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines, derived from 3-hydroxyisoindolinones has been demonstrated in this communication. A variety of isoindolinone-based α-amino diazo esters bearing a quaternary stereogenic center were afforded in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). Furthermore, the synthetic utility of the products has been depicted by the hydrogenation of the diazo moiety of adducts.

Graphical abstract: A chiral Brønsted acid-catalyzed highly enantioselective Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines

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Publication details

The article was received on 20 Feb 2018, accepted on 13 Mar 2018 and first published on 14 Mar 2018


Article type: Communication
DOI: 10.1039/C8CC01436A
Citation: Chem. Commun., 2018,54, 3516-3519
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    A chiral Brønsted acid-catalyzed highly enantioselective Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines

    R. A. Unhale, M. M. Sadhu, S. K. Ray, R. G. Biswas and V. K. Singh, Chem. Commun., 2018, 54, 3516
    DOI: 10.1039/C8CC01436A

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