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

This work reports new (4 + 2)-annulations of α-alkyl vinylgold carbenes with benzisoxazoles to afford 3,4-dihydroquinoline derivatives with high -stereoselectivity. The annulations are operable with carbenes in both acyclic and cyclic forms. This reaction sequence involves an initial formation of im...

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Bibliographic Details
Published in:	Chemical science (Cambridge) Vol. 9; no. 19; pp. 4488 - 4492
Main Authors:	Mokar, Bhanudas Dattatray, Jadhav, Prakash D, Pandit, Y B, Liu, Rai-Shung
Format:	Journal Article
Language:	English
Published:	England Royal Society of Chemistry 21-05-2018
Subjects:	Carbenes Carbonyls Derivatives Gold Imines Stereoselectivity Substrates
Online Access:	Get full text
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Summary:	This work reports new (4 + 2)-annulations of α-alkyl vinylgold carbenes with benzisoxazoles to afford 3,4-dihydroquinoline derivatives with high -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.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	2041-6520 2041-6539
DOI:	10.1039/c8sc00986d