Synthesis of ethyl (13E)-trifluoromethylretinoate and its analogues by palladium-catalysed cross-coupling

Authors
Thibonnet, J Prie, G Abarbri, M Duchene, A Parrain, JL
Citation
J. Thibonnet et al., Synthesis of ethyl (13E)-trifluoromethylretinoate and its analogues by palladium-catalysed cross-coupling, TETRAHEDR L, 40(16), 1999, pp. 3151-3154
Citations number
28
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
16
Year of publication
1999
Pages
3151 - 3154
Database
ISI
SICI code
0040-4039(19990416)40:16<3151:SOE(AI>2.0.ZU;2-Z
Abstract
Stereoselective construction of ethyl (13E)-trifluoromethylretinoate was ac hieved 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 wa s performed first and followed by iododestannylation. The second step invol ved another vinyltin which was synthetised by stannylmetallation of the Neg ishi dienyne 4c derived from beta-ionone, certain yne analogues were also p repared through Sonogashira coupling with 4c,d and ethyl 5-iodo-3-trifluoro methyl-pent-2,4-dienoate 3. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.