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Issue 17, 2019
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Catalytic asymmetric cycloaddition reactions of enoldiazo compounds

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Abstract

This review describes catalytic asymmetric cycloaddition reactions of silyl-protected enoldiazo compounds for the construction of highly functionalized carbo- and heterocycles which possess one or more chiral center(s). The enoldiazo compound or its derivative, donor–acceptor cyclopropene, form electrophilic vinylogous metal carbene intermediates that combine stepwise with nucleophilic dipolar reactants to form products from [3 + 1]-, [3 + 2]-, [3 + 3]-, [3 + 4]-, and [3 + 5]-cycloaddition, generally in high yield and with exceptional stereocontrol and regioselectivity.

Graphical abstract: Catalytic asymmetric cycloaddition reactions of enoldiazo compounds

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Article information


Submitted
26 Feb 2019
Accepted
22 Mar 2019
First published
22 Mar 2019

Org. Biomol. Chem., 2019,17, 4183-4195
Article type
Review Article
Author version available

Catalytic asymmetric cycloaddition reactions of enoldiazo compounds

K. O. Marichev and M. P. Doyle, Org. Biomol. Chem., 2019, 17, 4183
DOI: 10.1039/C9OB00478E

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