Issue 74, 2019

Mechanistic insights into the gold(i)-catalyzed annulation of propiolates with isoxazoles: a DFT study

Abstract

The detailed mechanisms of gold(I)-catalyzed annulations of propiolates with substituted and unsubstituted isoxazoles were investigated by DFT calculations. A unified rationale for the formation of the key seven-membered heterocyclic intermediate was proposed through initial chemoselective N-attack of isoxazole followed by sequential generation of an unprecedented 2H-azirine-containing intermediate, 6π electrocyclization and ring expansion. Subsequent substrate-dependent transformations were rationalized to generate the divergent products. The origins of the chemo- and regio-selectivities coupled with the factors responsible were addressed.

Graphical abstract: Mechanistic insights into the gold(i)-catalyzed annulation of propiolates with isoxazoles: a DFT study

Supplementary files

Article information

Article type
Communication
Submitted
05 jul 2019
Accepted
19 aug 2019
First published
20 aug 2019

Chem. Commun., 2019,55, 11127-11130

Mechanistic insights into the gold(I)-catalyzed annulation of propiolates with isoxazoles: a DFT study

A. A. Ogunlana and X. Bao, Chem. Commun., 2019, 55, 11127 DOI: 10.1039/C9CC05162G

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