Synthesis

A practical ex-chiral-pool synthesis of β-proline and homo-β-proline

C Thomas, F Orecher, P Gmeiner

Index: Thomas, Christoph; Orecher, Florian; Gmeiner, Peter Synthesis, 1998 , # 10 p. 1491 - 1496

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Citation Number: 18

Abstract

Abstract: Starting from aspartic acid an efficient synthesis of enantiomerically pure β-proline and homo-β-proline is described. The key step of the synthesis includes formation of the 1, 4- biselectrophile 6, followed by rearrangement via the aziridinium intermediate 7 and ring closure to give the pyrrolidinium salt 9a which can serve as a common precursor for both target compounds. Key words: β-proline, homo-β-proline, aziridinium intermediate, ...