Amino-zinc-ene-enolate cyclisation: a short access to (2S,3R)- and (2S,3S)-3-benzylprolines (3-benzylpyrrolidine-2-carboxylic acids) |
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Authors: | Jean Quancard |
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Affiliation: | UMR CNRS 7613, Structure et Fonction de Molécules Bioactives, Université Paris VI, case 45, 4 place Jussieu, 75252 Paris Cedex 05, France |
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Abstract: | The synthesis of 3-benzylprolines can be easily achieved in a diastereoselective and enantioselective way via amino-zinc-ene-enolate cyclisation. Transmetalation of the cyclic zinc intermediate with Pd2(dba)3/P(o-Tolyl)3 allowed functionalisation with an aromatic ring. One-pot hydrogenolysis and Boc-protection led to the cis-isomer readily usable for peptide synthesis. The trans-isomer was obtained by epimerisation of the α-centre in a sealed tube at 200 °C. |
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Keywords: | Amino-zinc-ene-enolate cyclisation |
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