Synthesis

Solvent-free Heck-Jeffery reactions under ball-milling conditions applied to the synthesis of unnatural amino acids precursors and indoles

E Tullberg, F Schacher, D Peters, T Frejd

Index: Tullberg, Erik; Schacher, Felix; Peters, Dan; Frejd, Torbjoern Synthesis, 2006 , # 7 p. 1183 - 1189

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Citation Number: 31

Abstract

Abstract The syntheses of various amino-and hydroxy-substituted dehydrophenylalanine derivatives using the Heck-Jeffery protocol under non-solvent conditions in a ball mill are presented. The influences of electron-withdrawing groups and of the location of the heteroatom substituent relative to the halide are discussed. Suitably substituted ortho-amino dehydrophenylalanine derivatives undergo a cyclization-elimination reaction to the ...

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