|
Hokkaido University Collection of Scholarly and Academic Papers >
Faculty of Pharmaceutical Sciences >
Peer-reviewed Journal Articles, etc >
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
| 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
|
