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

Nambu, Hisanori; Hikime, Mayuka; Krishnamurthi, Janagiraman; Kamiya, Megumi; Shimada, Naoyuki; Hashimoto, Shunichi

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

Nambu, Hisanori; Hikime, Mayuka; Krishnamurthi, Janagiraman et al.

Tetrahedron Letters, 2009, 50(26), 3675-3678

Permalink : https://hdl.handle.net/2115/38752

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アクセス権	open access
URI	https://hdl.handle.net/2115/38752
タイトル	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
著者	Nambu, Hisanori ; Hikime, Mayuka ; Krishnamurthi, Janagiraman ; Kamiya, Megumi ; Shimada, Naoyuki ; Hashimoto, Shunichi
e-Rad_Researcher 80399956 著者名 Nambu, Hisanori
著者名 Hikime, Mayuka
著者名 Krishnamurthi, Janagiraman
著者名 Kamiya, Megumi
著者名 Shimada, Naoyuki
e-Rad_Researcher 80107391 著者名 Hashimoto, Shunichi
言語	英語
キーワード	Carbonyl ylides
	1,3-Dipolar cycloadditions
	Chiral dirhodium(II) carboxylates
	Vindorosine
発行日	2009-07-01
出版者	Elsevier Ltd.
収録物名	Tetrahedron Letters
巻(号)	50(26)
ページ	3675-3678
抄録	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.
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
PISSN	0040-4039
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1016/j.tetlet.2009.03.142