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Synlett 2002(10): 1669-1672
DOI: 10.1055/s-2002-34224
LETTER
© Georg Thieme Verlag Stuttgart · New York

Regio- and Enantioselective Alkylation of a N-Protected Pyrrolidin-3-one Using Enders’ Chiral Hydrazone Method: A Key Step Towards a New Asymmetric Total Synthesis of (-)-Quinocarcin and Related Analogues

Uwe Schneider, Xavier Pannecoucke, Jean-Charles Quirion*
Laboratoire d’Hétérochimie Organique, Institut de Recherche en Chimie Organique Fine, Rue Lucien Tesnière, 76131 Mont-Saint-Aignan, France
Fax: +33(2)35522959; e-Mail: quirion@ircof.insa-rouen.fr;
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Publication History

Received 3 July 2002
Publication Date:
23 September 2002 (online)

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Abstract

The synthesis of C-4-alkylated pyrrolidin-3-one 5 was achieved by regio- and diastereoselective alkylation of chiral hydrazone 8 with electrophile 7 followed by selective deprotection. Highly functionalised compound 5 is the first key intermediate in our approach towards a new asymmetric total synthesis of (-)-quinocarcin (1) and related structural analogues 2 and 3.

Key words

alkylation - hydrazones - heterocycles - regioselectivity - stereoselectivity

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