Issue 19, 2018

Gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups

Abstract

This work reports new (4 + 2)-annulations of α-alkyl vinylgold carbenes with benzisoxazoles to afford 3,4-dihydroquinoline derivatives with high anti-stereoselectivity. The annulations are operable with carbenes in both acyclic and cyclic forms. This reaction sequence involves an initial formation of imines from α-alkylgold carbenes and benzisoxazoles, followed by a novel carbonyl-enamine reaction to yield 3,4-dihydroquinoline derivatives. This system presents the first alkyl C–H reactivity of α-alkyl gold carbenes with an external substrate.

Graphical abstract: Gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups

Supplementary files

Article information

Article type
Edge Article
Submitted
01 Mar 2018
Accepted
21 Apr 2018
First published
23 Apr 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 4488-4492

Gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups

B. D. Mokar, P. D. Jadhav, Y. B. Pandit and R. Liu, Chem. Sci., 2018, 9, 4488 DOI: 10.1039/C8SC00986D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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