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Synthesis 1994; 1994(12): 1322-1326
DOI: 10.1055/s-1994-25688
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Diastereo- and Enantioselective Synthesis of α- Substituted β-Amino Acid Esters by Tandem Michael-addition / α-Alkylation with TMS-SAMP as Chiral Equivalent of Ammonia

Dieter Enders* , Wolfgang Bettray, Gerhard Raabe, Jan Runsink
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet Straße 1, D-52074 Aachen, Germany
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Publication Date:
25 April 2002 (online)

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The hetero Michael-addition of (S)-(-)2-methoxymethyl-1-trimethylsilylaminopyrrolidine (TMS-SAMP) to α,β-unsaturated esters 1, followed by α-alkylation of the intermediate esterenolates with various electrophiles yields α-substituted β-hydrazino esters 3 of anti-configuration in good to excellent diastereomeric excesses (de = 63- ≥96 %). Subsequent reductive N-N bond cleavage leads to β-amino acid esters 4 (R1 = C6H11) in good yields and high diastereo and enantiomeric purity (de,ee ≥96 %). The stereochemistry was confirmed by NMR spectrocopy and X-ray structure analysis.