Gold-Catalyzed [3+2]-Annulations of α-Aryl Diazoketones with the Tetrasubstituted Alkenes of Cyclopentadienes: High Stereoselectivity and Enantioselectivity

Ching Nung Chen, Wei Min Cheng, Jian Kai Wang, Tzu Hsuan Chao, Mu Jeng Cheng, Rai Shung Liu

Research output: Contribution to journalArticlepeer-review

Abstract

This work reports gold-catalyzed [3+2]-annulations of α-diazo ketones with highly substituted cyclopentadienes, affording bicyclic 2,3-dihydrofurans with high regio- and stereoselectivity. The reactions highlights the first success of tetrasubstituted alkenes to undergo [3+2]-annulations with α-diazo carbonyls. The enantioselective annulations are also achieved with high enantioselectivity using chiral forms of gold and phosphoric acid. Our mechanistic analysis supports that cyclopentadienes serve as nucleophiles to attack gold carbenes at the more substituted alkenes, yielding gold enolates that complex with chiral phosphoric acid to enhance the enantioselectivity.

Original languageEnglish
Pages (from-to)4479-4484
Number of pages6
JournalAngewandte Chemie - International Edition
Volume60
Issue number9
DOIs
Publication statusPublished - 2021 Feb 23

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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