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Design and synthesis of hydrophobic, bulky χ2-constrained phenylalanine and naphthylalanine derivatives

✍ Scribed by Wei Wang; Junyi Zhang; Chiyi Xiong; Victor J. Hruby

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
129 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

A series of novel hydrophobic, bulky x 2 -constrained phenylalanine and naphthylalanine derivatives were designed and synthesized. Asymmetric hydrogenations of a-enamides using Burk's DuPHOS-based Rh(I) catalysts generated high enantiomerically pure a-amino acid derivatives, which subsequently underwent Suzuki cross couplings with boronic acid derivatives to afford these aromatic substituted amino acids in high yields and with high enantioselectivity.

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