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
- 1 April 1995
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1995 (04) , 369-371
- https://doi.org/10.1055/s-1995-4953
Abstract
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.Keywords
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