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 language | English |
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Pages (from-to) | 4479-4484 |
Number of pages | 6 |
Journal | Angewandte Chemie - International Edition |
Volume | 60 |
Issue number | 9 |
DOIs | |
Publication status | Published - 2021 Feb 23 |
All Science Journal Classification (ASJC) codes
- Catalysis
- Chemistry(all)