Access to Cyclic α‐CF3‐Substituted α‐Amino Acid Derivatives by Ring‐Closing Metathesis of Functionalized 1, 7‐Enynes. Issue 24 (10th July 2013)

• Record Type: Journal Article
• Authors: Mailyan, Artur K.; Krylov, Ivan M.; Bruneau, Christian; Dixneuf, Pierre H.; Osipov, Sergey N.
• Is Part Of: European journal of organic chemistry. Issue 24(2013)
• Page Start: 5353
• Page End: 5363
• Publication Date: 2013-07-10
• Subjects: Amino acids -- Enynes -- Metathesis -- Cyclization -- Cross‐coupling -- Fluorine; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300619
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: An efficient method for the preparation of new α‐CF3 α‐amino acid 1, 7‐enynes that contain electron‐donating and electron‐withdrawing groups on the triple bond has been developed that proceeds through a Sonogashira‐type coupling reaction. The ring‐closing enyne methathesis (RCEYM) of the obtained 1, 7‐enynes with commercially available Grubbs and Hoveyda catalysts provides access to a series of new cyclic α‐amino acids. The latter compounds that contain the 1, 3‐diene moiety are attractive building blocks for the construction of trifluoromethylated polycyclic systems. Abstract : An efficient method to prepare new α‐CF3 α‐amino acid 1, 7‐enynes that contain different substituents on the triple bond has been developed that proceeds by a Sonogashira‐type coupling reaction. The ring‐closing enyne methathesis (RCEYM) of the obtained 1, 7‐enynes with commercially available Grubbs and Hoveyda catalysts provides access to a series of new cyclic α‐amino acids.