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A Concise highly enantioselective cascade synthesis of indolizidine alkaloids with a quaternary stereocenter

Muroni, Daniele and Saba, Antonio and Culeddu, Nicola (2004) A Concise highly enantioselective cascade synthesis of indolizidine alkaloids with a quaternary stereocenter. Tetrahedron: Asymmetry, Vol. 15 (17), p. 2609-2614. ISSN 0957-4166. Article.

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DOI: 10.1016/j.tetasy.2004.07.013

Abstract

Enantiomerically pure indolizidinones bearing a quaternary stereocenter were obtained by Rh(II)-catalyzed decomposition of α-diazo ketodiesters through a carbenoid/spiro[5,5]ammonium ylide/Stevens [1,2]-shift with a ring-expansion cascade process. The isolation of stable chiral ammonium ylides, namely the key intermediates of the process, unambiguously confirmed the stereochemistryof the total process.

Item Type:Article
ID Code:1969
Status:Published
Refereed:Yes
Uncontrolled Keywords:Rhodiumbased catalysis, ammonium ylides, [1,2]-Stevens, complex alkaloids
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:Pergamon / Elsevier
ISSN:0957-4166
Copyright Holders:© 2004 Elsevier
Deposited On:18 Aug 2009 10:06

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