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Synthesis and reactions of fluorous carbobenzyloxy (fCbz) derivatives of α-amino acids

Curran, DP and Amatore, M and Guthrie, D and Campbell, M and Go, E and Luo, Z (2003) Synthesis and reactions of fluorous carbobenzyloxy (fCbz) derivatives of α-amino acids. Journal of Organic Chemistry, 68 (12). 4643 - 4647. ISSN 0022-3263

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Abstract

Fluorous carbobenzyloxy (FCbz) reagents RfCH2CH2C6H4CH2 OC(O)OSu (where Su is succinimidoyl and Rf is C6F13 and C8F17) have been used to make FCbz derivatives of 18 of the 20 natural amino acids. The potential utility of this new family of reagents in both standard fluorous synthesis with spe separation and fluorous quasiracemic synthesis is illustrated with representative reactions of the FCbz-Phe derivatives.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Curran, DPcurran@pitt.eduCURRAN
Amatore, M
Guthrie, D
Campbell, M
Go, E
Luo, Z
Date: 13 June 2003
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 68
Number: 12
Page Range: 4643 - 4647
DOI or Unique Handle: 10.1021/jo0344283
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Amino Acids--chemistry; Benzene Derivatives--chemical synthesis; Benzene Derivatives--chemistry; Catalysis; Chromatography, High Pressure Liquid; Fluorides--chemical synthesis; Fluorides--chemistry; Indicators and Reagents; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Stereoisomerism
PubMed ID: 12790566
Date Deposited: 30 Jan 2014 17:01
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/20428

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