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

Philip A. P. Reeve | Zendy; Urszula Grabowska | Zendy; Lourdes Salvador Oden | Zendy; Daniel Wiktelius | Zendy; Fredrik Wångsell | Zendy; Richard F. W. Jackson | Zendy

Open Access

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

Author(s) -

Philip A. P. Reeve,

Urszula Grabowska,

Lourdes Salvador Oden,

Daniel Wiktelius,

Fredrik Wångsell,

Richard F. W. Jackson

Publication year - 2019

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.9b01509

Subject(s) - side chain , selectfluor , amino acid , chemistry , surface modification , catalysis , organic chemistry , biochemistry , polymer

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)/NaBH 4 and Selectfluor. The modification of the conditions by replacement of Selectfluor with NaN 3 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.

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