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Asymmetric approach to the pentacyclic skeleton of Aspidosperma alkaloids via enantioselective intramolecular 1,3-dipolar cycloaddition of carbonyl ylides catalyzed by chiral dirhodium(II) carboxylates

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Title: Asymmetric approach to the pentacyclic skeleton of Aspidosperma alkaloids via enantioselective intramolecular 1,3-dipolar cycloaddition of carbonyl ylides catalyzed by chiral dirhodium(II) carboxylates
Authors: Nambu, Hisanori Browse this author →KAKEN DB
Hikime, Mayuka Browse this author
Krishnamurthi, Janagiraman Browse this author
Kamiya, Megumi Browse this author
Shimada, Naoyuki Browse this author
Hashimoto, Shunichi Browse this author →KAKEN DB
Keywords: Carbonyl ylides
1,3-Dipolar cycloadditions
Chiral dirhodium(II) carboxylates
Vindorosine
Issue Date: 1-Jul-2009
Publisher: Elsevier Ltd.
Journal Title: Tetrahedron Letters
Volume: 50
Issue: 26
Start Page: 3675
End Page: 3678
Publisher DOI: 10.1016/j.tetlet.2009.03.142
Abstract: This paper 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 an 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], Rh2(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 π-bond.
Type: article (author version)
URI: http://hdl.handle.net/2115/38752
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 南部 寿則

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