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Asymmetric Synthesis of Cyclic Fluorinated Amino Acids
Author(s) -
Hao Jing,
Milcent Thierry,
Retailleau Pascal,
Soloshonok Vadim A.,
Ongeri Sandrine,
Crousse Benoit
Publication year - 2018
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/ejoc.201800255
Subject(s) - chemistry , intramolecular force , proline , amino acid , ring closing metathesis , metathesis , stereochemistry , ring (chemistry) , enantioselective synthesis , organic chemistry , catalysis , polymerization , biochemistry , polymer
A methodology for the asymmetric synthesis of CF 3 ‐β‐proline and CF 3 ‐six‐membered cyclic amino acids has been developed starting from readily available N ‐ tert ‐butanesulfinyl‐(3,3,3)‐trifluoroacetaldimine. The Zn‐mediated allylation followed by an intramolecular 5‐ endo ‐ trig cyclisation afforded the CF 3 ‐β‐proline, whereas the CF 3 ‐six‐membered cyclic amino acids were obtained by using a ring‐closing‐metathesis protocol of CF 3 ‐aminodienes.
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