Premium
Synthesis of Enantiomerically Pure Amino Acids Containing 2,5‐Disubstituted THF Rings in the Molecular Backbone
Author(s) -
Schrey Anna,
Osterkamp Frank,
Straudi Alrun,
Rickert Corry,
Wagner Holger,
Koert Ulrich,
Herrschaft Bernhard,
Harms Klaus
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199911)1999:11<2977::aid-ejoc2977>3.0.co;2-3
Subject(s) - chemistry , intramolecular force , epoxide , ketone , stereochemistry , amino acid , alanine , cis–trans isomerism , medicinal chemistry , organic chemistry , catalysis , biochemistry
N ‐ and C ‐protected derivatives of 2,5‐disubstituted trans ‐ and cis ‐THF amino acids 6 and 7 were prepared in enantiomerically pure form from L ‐alanine. Felkin–Anh‐controlled reduction of the ketone 9 was achieved with a 85:15 diastereoselectivity. Epoxidation of 10 and subsequent intramolecular epoxide opening gave the trans ‐ and cis ‐THF alcohols 11 and 12 , which were further transformed into the corresponding N ‐ and C ‐protected 2,5‐disubstituted trans ‐ and cis ‐THF amino acids. Conformational studies show that the cis ‐THF diamide 34 is a β‐turn mimetic in the solid state and in CDCl 3 solution.