Synthesis 2005(1): 75-84  
DOI: 10.1055/s-2004-834917
PAPER
© Georg Thieme Verlag Stuttgart · New York

Nucleophilic Addition of α-Metallated Carbamates to Planar Chiral Cationic η3-Allylmolybdenum Complexes: A Stereochemical Study

Philip J. Kocienski*a, John A. Christopherb,c, Richard Bellc, Bernhard Ottoa
a Department of Chemistry, Leeds University, Leeds LS2 9JT, UK
Fax: +44(113)3436401; e-Mail: p.kocienski@chemistry.leeds.ac.uk;
b Department of Chemistry, Glasgow University, Glasgow G12 8QQ, UK
c GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage SG1 2NY, UK
Further Information

Publication History

Received 9 September 2004
Publication Date:
17 November 2004 (online)

Abstract

Chiral α-(O-carbamoyl)alkyl- and α-(N-carbamoyl)al­kylcopper(I) reagents derived from (-)-sparteine-mediated asymmetric lithiation of hindered carbamates react with cationic η3-allylmolybdenum complexes with retention of configuration.

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Attempts to accomplish a similar enzymatic resolution of (±)-33 failed.

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The supplementary crystallographic data for this structure (CCDC 247732) can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.