Synthesis p. 1322 - 1326 (1994)
Update date:2022-08-11
Topics:
Enders
Bettray
Raabe
Runsink
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-spectroscopy and X-ray structure analysis.
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