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Issue 40, 2017
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Unique site-selectivity control in asymmetric Michael addition of azlactone to alkenyl dienyl ketones enabled by P-spiro chiral iminophosphorane catalysis

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Abstract

A highly regio-, diastereo-, and enantioselective 1,6-addition of azlactone to various alkenyl dienyl ketones has been achieved under P-spiro chiral triaminoiminophosphorane catalysis. This site-selectivity control relies on the distinct ability of the conjugate acids of iminophosphoranes, aminophosphonium ions, to precisely differentiate between the three electrophilic reaction sites of alkenyl dienyl ketones, which is further demonstrated by the discriminative asymmetric 1,6-addition of azlactone to dienyl ketones, leaving the coexisting alkenyl ketone intact.

Graphical abstract: Unique site-selectivity control in asymmetric Michael addition of azlactone to alkenyl dienyl ketones enabled by P-spiro chiral iminophosphorane catalysis

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Publication details

The article was received on 06 Mar 2017, accepted on 20 Apr 2017 and first published on 20 Apr 2017


Article type: Communication
DOI: 10.1039/C7CC01715D
Citation: Chem. Commun., 2017,53, 5495-5498
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    Unique site-selectivity control in asymmetric Michael addition of azlactone to alkenyl dienyl ketones enabled by P-spiro chiral iminophosphorane catalysis

    K. Yoshioka, K. Yamada, D. Uraguchi and T. Ooi, Chem. Commun., 2017, 53, 5495
    DOI: 10.1039/C7CC01715D

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