Journal
TETRAHEDRON LETTERS
Volume 50, Issue 26, Pages 3675-3678Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.03.142
Keywords
Carbonyl ylides; 1,3-Dipolar cycloadditions; Chiral dirhodium(II) carboxylates; Vindorosine
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Funding
- Grants-in-Aid for Scientific Research [20390002] Funding Source: KAKEN
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This Letter describes asymmetric tandem carbonyl ylide formation-intramolecular 1,3-dipolar cycloaddition reaction of diazo imides containing a tethered indole catalyzed by chiral dirhodium(II) carboxylates as ail approach to the pentacyclic skeleton of Aspidosperma alkaloids. The cycloaddition of carbonyl ylides derived from indolyl-substituted 2-diazo-5-imido-3-ketoesters Under the influence of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-]leucinate], Rh-2(S-TCPTTL)(4), provides cycloadducts in moderate yields and enantioselectivities of up to 66% ee as well as with perfect endo diastereoselectivity. This is the first example of asymmetric induction in an intramolecular cycloaddition of a carbonyl ylide across an indolyl pi-bond. (C) 2009 Elsevier Ltd. All rights reserved.
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