Synthesis 1997; 1997(3): 313-327
DOI: 10.1055/s-1997-4465
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Asymmetric Synthesis of α-Alkyl-ω-amino Acids and α-Alkyllactams

Antje Rottmann1 , M. Bartoczek2 , Jürgen Liebscher3
  • 1Institut für Chemie, Humboldt-Universität Berlin, Hessische Str. 1-2, D-10115 Berlin, Germany
  • 2Institut für Angewandte Chemie, Rudower Chausse 5, D-12484 Berlin, Germany
  • 3Institut für Chemie, Humboldt-Universität Berlin, Hessische Str. 1-2, D-10115 Berlin, Germany, Fax +49(30)20937343; E-mail liebscher@chemie.hu-berlin.de
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Publikationsdatum:
31. Dezember 2000 (online)

A versatile access to optically active α-branched ω-amino acids 8 and 9 and corresponding lactams 11 was developed allowing the synthesis of either enantiomer of these products. This asymmetric synthesis is based on amino alcohols 3 as chiral auxiliaries, which were converted to 2-(ω-benzenesulfonylaminoalkyl)oxazolines 4 by reaction with ω-amino-imido esters 2 or derivatives of lactams 1. The 2-(ω-benzenesulfonylaminoalkyl)oxazolines 4 were deprotonated by LDA and α-alkylated by alkyl halides 5. Final hydrolytic cleavage of the oxazoline ring afforded the amino acids 8 and 9 or lactams 11. The method does not follow Meyers model of α-alkylation of 2-alkyloxazolines and requires BEt3 as additive in order to achieve complete stereoselectivity.