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Synthesis and Transformations of Novel L ‐Phenylalanine Derived Pyrazolidin‐3‐ones
Author(s) -
Grošelj Uroš,
Golobič Amalija,
Svete Jurij,
Stanovnik Branko
Publication year - 2013
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22166
Subject(s) - chemistry , stereocenter , diastereomer , chirality (physics) , stereochemistry , thiourea , phenylalanine , absolute configuration , bicyclic molecule , enantioselective synthesis , amino acid , organic chemistry , catalysis , biochemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark
A simple and straightforward four‐step synthesis of novel diastereomeric L‐phenylalanine‐derived pyrazolidin‐3‐ones is described. The absolute configuration of the novel C(5) stereogenic centre has been unambiguously determined by single crystal X‐ray analysis and via chemical interconversions. A series of novel thiourea derived pyrazolidinones have been prepared and tested as potential organocatalysts. N(1) un‐substituted pyrazolidinones can be used for the construction of a novel type of bicyclic heterocycles and other selective derivatizations. Chirality 25:541–555, 2013 . © 2013 Wiley Periodicals, Inc.