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Synlett 1997; 1997(7): 789-790
DOI: 10.1055/s-1997-5769
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Stereospecific Allylation of a Serine-derived Zinc/Copper Reagent. Synthesis of Substituted Pipecolic Acid Derivatives

Richard F.W. Jackson1 , Debra Turner2 , Michael H. Block3
  • 1Department of Chemistry, Bedson Building, The University of Newcastle, Newcastle upon Tyne, NE1 7RU, UK, E-mail: r.f.w.jackson@newcastle.ac.uk
  • 2Department of Chemistry, Bedson Building, The University of Newcastle, Newcastle upon Tyne, NE1 7RU, UK
  • 3Zeneca Pharmaceuticals, Mereside, Alderley Park, Macclesfield, Cheshire SK10 4TG, UK
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Publication History

Publication Date:
31 December 2000 (online)

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Serine-derived zinc/copper reagents 1 and 2 add to enantiomerically pure (η3-allyl)iron tetracarbonyl salts in fair to good yield in a stereospecific fashion. The vinylsulfones 10-12 can be converted into 4-methylpipecolic acid derivatives 19-21 in a two-step process comprising epoxidation and Zn/TMSCl mediated cyclisation.

α-amino acids - organozinc reagents - (η3-allyl)iron tetracarbonyl salts - pipecolic acids