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Issue 9, 1994
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Asymmetric synthesis of anti-α-alkyl-β-amino acids


An investigation into the asymmetric induction accompanying alkylations of enolates derived from the highly diastereoselective conjugate addition of lithium (R)-N-benzyl-N-α-methylbenzylamide (R)-1 to crotonate and cinnamate esters has been performed. The access to different enolate geometries afforded by the conjugate addition process and subsequent enolate regeneration by deprotonation of the β-amino ester conjugate adducts enabled two disparate sets of selectivity data to be compiled. Although both approaches furnished predominantly anti-α-alkyl-β-amino esters, the two-step procedure proved to be considerably more selective. Several factors which play a major role in determining the alkylation selectivity are identified, including the cooperative influence of the α-methylbenzylamino stereocentre. Since debenzylation and hydrolysis of the alkylated products was straightforward, this methodology provides a direct route to anti-α-alkyl-β-amino acids in homochiral form.

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Article type: Paper
DOI: 10.1039/P19940001129
Citation: J. Chem. Soc., Perkin Trans. 1, 1994,0, 1129-1139
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    Asymmetric synthesis of anti-α-alkyl-β-amino acids

    S. G. Davies and I. A. S. Walters, J. Chem. Soc., Perkin Trans. 1, 1994, 0, 1129
    DOI: 10.1039/P19940001129

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