PDF herunterladen
Synlett 1995; 1995(4): 369-371
DOI: 10.1055/s-1995-4953
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Diastereo- and Enantioselective Synthesis of trans-2-Amino-Cycloalkane-1-Carboxylic Acids via Intramolecular Tandem Michael-Addition/α-Alkylation Using TMS-SAMP as Chiral Equivalent of Ammonia

Dieter Enders* , Jürgen Wiedemann, Wolfgang Bettray
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

trans-2-amino cyclopentane-, cyclohexane- and cycloheptane-1-carboxylic acids of high diastereo- and enantiomeric purity (de ≥ 96-98%, ee ≥ 98%) are prepared utilizing the stereoselective conjugate addition of lithiated (S)-(-)-2-methoxymethyl-1-trimethylsilylamino-pyrrolidine (TMS-SAMP) to ω-halide substituted α,β-unsaturated enoates followed by subsequent ring closure of the intermediate ester enolate (MIRC-reaction). The auxiliary is removed by reductive N-N bond cleavage.

β-amino acids - Michael initiated ring closure - TMS-SAMP - nitrogen-nucleophile - asymmetric synthesis