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Catalytic enantioselective [3 + 2]-cycloadditions of diazoketone-derived aryl-substituted carbonyl ylides

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Abstract

An evaluation of α-aryl-α-diazodiones in tandem carbonyl ylide formation−enantioselective [3 + 2]-cycloaddition reactions is described. Such substrates were designed to allow investigation of the electronic characteristics of the dipole upon asymmetric induction. Intramolecular cycloadditions (with a tethered alkene dipolarophile) were found to occur in good to quantitative yields, with a difference in ee exhibited by the two electronically different diazodiones 8 and 9. Intermolecular cycloadditions using diazodiones 12 and 13 with DMAD and arylacetylenes 16−18 again demonstrated that electronics play a key role in determining the outcome of the cycloaddition reactions. Enantioselectivities of up to 76% were observed.

Publication Information

Output type

Research Output:
Contribution to journal
Article
 Peer-review

Original language

English

Journal (Volume, Issue Number)

Journal of Organic Chemistry

Publication milestones

  • Published - 01/01/2003

Publication status

Published - 01/01/2003

ISSN

0022-3263

Publication IDs

  • handle.net: 10547/302107
  • Scopus: 0037462399

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