Radical Functionalization of Unsaturated Amino Acids: Synthesis of Side-Chain-Fluorinated, Azido-Substituted, and Hydroxylated Amino Acids

Radical Functionalization of Unsaturated Amino Acids : Synthesis of Side-Chain-Fluorinated, Azido-Substituted, and Hydroxylated Amino Acids

A range of enantiomerically pure protected side-chain-fluorinated amino acids has been prepared (13 examples) by treatment of protected amino acids containing unsaturated side chains with a combination of Fe(III)/NaBH4 and Selectfluor. The modification of the conditions by replacement of Selectfluor with NaN3 allowed the preparation of side-chain azido-substituted amino acids (five examples), which upon catalytic hydrogenation gave the corresponding amines, isolated as lactams (four examples). Radical hydration of the unsaturated side chains leading to side-chain-hydroxylated protected amino acids has also been demonstrated.

Grabowska, U.Medivir AB, Sweden; F-star Biotechnology Ltd, UK (author)
Oden, L. S.Medivir AB, Sweden (author)
Wiktelius, D.Medivir AB, Sweden; FOI Swedish Defence Research Agency, Sweden (author)
Wångsell, FredrikRISE,Kemi och material,Medivir AB, Sweden (author)
Jackson, R. F. W.University of Sheffield, Uk (author)
University of Sheffield, UkMedivir AB, Sweden; F-star Biotechnology Ltd, UK (creator_code:org_t)

By the author/editor: Reeve, P. A. P.; Grabowska, U.; Oden, L. S.; Wiktelius, D.; Wångsell, Fredri ...; Jackson, R. F. W ...

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