Gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups. Issue 19 (30th April 2018)

• Record Type: Journal Article
• Authors: Mokar, Bhanudas Dattatray; Jadhav, Prakash D.; Pandit, Y. B.; Liu, Rai-Shung
• Is Part Of: Chemical science. Volume 9:Issue 19(2018)
• Page Start: 4488
• Page End: 4492
• Publication Date: 2018-04-30
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c8sc00986d
• Languages: English
• ISSNs: 2041-6520

Abstract

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. 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.