499201-16-0Relevant academic research and scientific papers
Catalytic enantioselective [3 + 2]-cycloadditions of diazoketone-derived aryl-substituted carbonyl ylides
Hodgson, David M.,Glen, Rebecca,Grant, Guy H.,Redgrave, Alison J.
, p. 581 - 586 (2003)
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.
[3+2] Cycloaddition reactions of arylacetylenes with carbonyl ylides derived from 1-aryl-1-diazohexane-2,5-diones
Hodgson, David M.,Glen, Rebecca,Redgrave, Alison J.
, p. 3927 - 3930 (2007/10/03)
The synthesis and 1,3-dipolar cycloaddition reactions of α-aryl-α-diazodiones with aryl acetylenes (up to 76% ee) are described.
