Issue 40, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
06 Mar 2017
Accepted
20 Apr 2017
First published
20 Apr 2017

Chem. Commun., 2017,53, 5495-5498

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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