Journal
TETRAHEDRON-ASYMMETRY
Volume 16, Issue 24, Pages 4022-4033Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2005.10.015
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All stereoisomers of 1-amino-2-phenylcyclobutanecarboxylic acid-c(4)Phe-have been synthesized and the series c(n)Phe has thus been completed. The use of two different strategies based on a cyclization reaction, starting from ethyl isocyanoacetate and dialkyl malonate, respectively, gave both cis-c(4)Phe and trans-c(4)Phe in racemic form. HPLC resolution of one of the intermediates using a cellulose-derived chiral stationary phase allowed the isolation of the corresponding enantiomerically pure N-protected amino acids, prepared for incorporation into peptides. The relative stereochemistry of enantiopure compounds has been unambiguously assigned. (c) 2005 Elsevier Ltd. All rights reserved.
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