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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

IMPACT FACTOR 2018: 0.961

CiteScore 2018: 0.91

SCImago Journal Rank (SJR) 2018: 0.263
Source Normalized Impact per Paper (SNIP) 2018: 0.505

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Volume 69, Issue 11-12


Enantioselective Synthesis and Photoreactivity of a Diazirinyl-substituted (R)-β-Phenylalanine

Jan-Niklas Schäckermann / Thomas Lindel
Published Online: 2015-03-19 | DOI: https://doi.org/10.5560/znb.2014-4152


The first enantioselective synthesis of a photoreactive (R)-β-phenylalanine is described. In the key step, m-diazirinyl-substituted benzaldehyde is converted to a chiral sulfinimine in a Ti(OEt)4- mediated reaction, followed by diastereoselective enolate addition. The absolute configuration of photo (R)-β-phenylalanine was confirmed by Mosher analysis. The photo amino acid proved to be thermally stable under standard laboratory conditions. Irradiation in toluene afforded cycloheptatriene=norcaradiene valence tautomers, together with carbene benzylation. Quantumchemical calculations indicate a small triplet-singlet gap.

Keywords: Amino Acids; Diazirines; Photochemistry; Carbenes; DFT Calculation

About the article

Received: 2014-07-11

Published Online: 2015-03-19

Published in Print: 2014-12-01

Citation Information: Zeitschrift für Naturforschung B, Volume 69, Issue 11-12, Pages 1088–1096, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.5560/znb.2014-4152.

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© 1946 – 2014: Verlag der Zeitschrift für Naturforschung.

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