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The Photochemistry of N ‐Phthaloyl α‐Amino Acid Esters: A New Approach to β,γ‐Unsaturated α‐Amino Acids and Dihydrobenzazepinediones
Author(s) -
Griesbeck Axel G.,
Mauder Harald
Publication year - 1992
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199200731
Subject(s) - diradical , chemistry , derivative (finance) , amino acid , leucine , valine , carboxylate , medicinal chemistry , stereochemistry , biochemistry , physics , nuclear physics , singlet state , financial economics , economics , excited state
Interesting as enzyme inhibitors, β,γ‐unsaturated α‐amino acids can be synthesized by irradiation of the corresponding N ‐phthaloyl methyl ester [Reaction (a)]. Apart from this reaction, two further reaction pathways are observed (except in the case of the valine derivative): In the absence of γ H atoms, as in the tert ‐leucine derivative, the 1,5‐diradical cyclization and the formation of dihydrobenzazepinedione carboxylate, presumably via an ϵ‐Norrish type II intermediate. R 1 = H, Me, Et.