Enantioselective synthesis of 4-substituted phenylalanines by cross-coupling reactions

• Published in: Tetrahedron letters Vol. 40; no. 2; pp. 213 - 216
• Main Authors: Firooznia, Fariborz, Gude, Candido, Chan, Kenneth, Marcopulos, Nicholas, Satoh, Yoshitaka
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01-01-1999
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/S0040-4039(98)02272-2

The enantiomerically enriched BOC-protected (4-pinacolylborono)phenylalanine methyl ester (
8) is produced via enzymatic resolution of the racemic material, or direct synthesis from the corresponding iodide (or triflate), and undergoes Suzuki-Miyaura coupling reactions with aromatic halides and triflates in the presence of catalytic amounts of PdCl
2(dppf) to produce enantiomerically enriched 4-substituted phenylalanine derivatives.
The enantiomerically enriched BOC-protected (4-pinacolylborono)phenylalanine methyl ester is produced via enzymatic resolution of the racemic material, or direct synthesis from the corresponding iodide (or triflate), and undergoes Suzuki-Miyaura coupling reactions with aromatic halides and triflates in the presence of catalytic amounts of PdCl
2(dppf) to produce enantiomerically enriched 4-substituted phenylalanine derivatives.
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