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Synlett 1995; 1995(4): 369-371
DOI: 10.1055/s-1995-4953
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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
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Publication History

Publication Date:
31 December 2000 (online)

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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

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