Application of asymmetric phase-transfer catalysis in the enantioselective synthesis of cis-5-substituted proline esters

作者：Lygo Barry^*; Beynon Christopher; McLeod Michael C; Roy Claude Eric; Wade Charles E

来源：Tetrahedron, 2010, 66(46): 8832-8836.

DOI：10.1016/j.tet.2010.09.075

• Asymmetric catalysis
• Michael addition
• Hydrogenation
• Amino acids
• Pyrrolidines

A simple, highly stereoselective three-step sequence for the enantioselective synthesis of cis-5-substituted praline esters is described. This sequence features an asymmetric PTC Michael addition, followed by acid catalysed imine exchange and catalytic hydrogenation. Application of this chemistry in the synthesis of the nonpeptide cholecystokinin antagonist (+)-RP-66803 11 is also described.

• 出版日期2010-11-13