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

Journal article

An evaluation of alpha-aryl-alpha-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.

Authors: Hodgson, D; Glen, R; Grant, G; Redgrave, A

• Publication status: Published
• Journal: Journal of organic chemistry
• Volume: 68
• Issue: 2
• Pages: 581-586
• Publication date: 2003-01-01
• DOI: 10.1021/jo026307t
• EISSN: 1520-6904
• ISSN: 0022-3263
• Language: English