A Simple and General Chiral Silicon Lewis Acid for Asymmetric Synthesis:  Highly Enantioselective [3 + 2] Acylhydrazone−Enol Ether Cycloadditions

A Simple and General Chiral Silicon Lewis Acid for Asymmetric Synthesis:  Highly Enantioselective [3 + 2] Acylhydrazone−Enol Ether Cycloadditions

A highly diastereo- and enantioselective [3 + 2] acylhydrazone−enol ether cycloaddition mediated by a simple chiral silane Lewis acid is described. The reactions are highly practical, as demonstrated by a larger scale (5 g of the hydrazone) reaction in which the product was obtained after recrystall...

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Veröffentlicht in:Journal of the American Chemical Society 2005-07, Vol.127 (28), p.9974-9975
Hauptverfasser: Shirakawa, Seiji, Lombardi, Pamela J, Leighton, James L
Format: Artikel
Sprache:eng
Schlagworte:
Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
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Zusammenfassung:A highly diastereo- and enantioselective [3 + 2] acylhydrazone−enol ether cycloaddition mediated by a simple chiral silane Lewis acid is described. The reactions are highly practical, as demonstrated by a larger scale (5 g of the hydrazone) reaction in which the product was obtained after recrystallization in 93% yield and 99% ee. Evidence for a stepwise mechanism and a model for the asymmetric induction are presented, as well.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja052307+