Enantioselective Catalytic Intramolecular Cyclopropanation using Modified Cinchona Alkaloid Organocatalysts

A mechanism‐guided design process was used to develop cinchona alkaloids that are substituted at the C2′ position of the quinoline moiety. These compounds prove to be excellent organocatalysts for an enantioselective intramolecular cyclopropanation reaction (see scheme).

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Bibliographic Details
Published in:	Angewandte Chemie International Edition Vol. 45; no. 36; pp. 6024 - 6028
Main Authors:	Johansson, Carin C. C., Bremeyer, Nadine, Ley, Steven V., Owen, Dafydd R., Smith, Stephen C., Gaunt, Matthew J.
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 11-09-2006 WILEY‐VCH Verlag
Subjects:	Alkenes - chemical synthesis Alkenes - chemistry asymmetric synthesis Catalysis cinchona alkaloids Cinchona Alkaloids - chemistry cyclopropanation Cyclopropanes - chemistry Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry intramolecular reactions Models, Chemical Molecular Conformation Molecular Structure Organic Chemicals - chemistry organocatalysis Stereoisomerism
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Description
Summary:	A mechanism‐guided design process was used to develop cinchona alkaloids that are substituted at the C2′ position of the quinoline moiety. These compounds prove to be excellent organocatalysts for an enantioselective intramolecular cyclopropanation reaction (see scheme).
Bibliography:	We gratefully acknowledge Pfizer Ltd (Sandwich) for a PhD studentship (C.C.C.J.), Syngenta for a Case Award (N.B.), Novartis for a Research Fellowship (S.V.L.), the Royal Society for University Research Fellowship (M.J.G.), and the EPSRC Mass Spectrometry service at the University of Swansea. ArticleID:ANIE200602129 Royal Society for University Research Fellowship ark:/67375/WNG-8RJFXCCZ-W istex:D57F09C4A70D6D1A7A32163057E74D68B48D7549 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.200602129