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

Chem Sci

Frontier Research Centers for Materials Science and Technology , Department of Chemistry , National Tsing-Hua University, Hsinchu , Taiwan , Republic of China . Email:

Published: May 2018

AI Article Synopsis

  • This study introduces a new (4 + 2)-annulation reaction involving α-alkyl vinylgold carbenes and benzisoxazoles, successfully producing 3,4-dihydroquinoline derivatives with high stereoselectivity.
  • The reaction can be performed with both acyclic and cyclic forms of the carbenes.
  • It highlights the innovative carbonyl-enamine reaction and marks the first instance of alkyl C-H reactivity in α-alkyl gold carbenes interacting with an external substrate.

Article Abstract

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.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6049024PMC
http://dx.doi.org/10.1039/c8sc00986dDOI Listing

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