J. Thibonnet, G. Prié, M. Abarbri
Apr 16, 1999
Citations
0
Influential Citations
26
Citations
Journal
Tetrahedron Letters
Abstract
Abstract Stereoselective construction of ethyl (13 E )-trifluoromethylretinoate was achieved through two successive Stille reactions. The coupling of ( E )-1,2-bis(tributylstannyl)ethene and ethyl ( Z )-4,4,4-trifluoro-3-iodobut-2-enoate was performed first and followed by iododestannylation. The second step involved another vinyltin which was synthetised by stannylmetallation of the Nigishi dienyne 4c derived from β-ionone. Certain yne analogues were also prepared through Sonogashira coupling with 4c,d and ethyl 5-iodo-3-trifluoromethyl-pent-2,4-dienoate 3 .