3
References and notes
1.
For a general overview, see: Hofmann, E., Klimisch, H.-J., Backes, R.,
Vogelsang, R., Franz, L.; Feuerhake, R. in Ullmann's Encyclopedia of
Industrial Chemistry, Wiley VCH, Weinheim, 2011; Vol. 38, pp 125-
132.
2.
3.
Rehbein, J., Hiersemann, M. Synthesis 2013, 1121-1159.
(a) He, W.; Herrick, I.; Atesin, T.; Caruana, P.; Kellenberger, C.;
Frontier, A. J. Am. Chem. Soc. 2008, 130, 1003-1011. (b) Malona, J.;
Cariou, K.; Frontier, A. J. Am. Chem. Soc. 2009, 131, 7560-7561.
Boger, D. L.; Ichikawa, S.; Jiang, H. J. Am. Chem. Soc. 2000, 122,
12169-12173.
4.
5.
6.
Aoshima, S.; Kanaoka, S. Chem. Rev. 2009, 109, 5245-5287.
For a review, see: Winternheimer, D. J.; Shade, R. E.; Merlic, C. A.
Synthesis 2010, 2497-2511.
7.
For examples, see: (a) Surprenant, S.; Chan, W. Y.; Berthelette, C. Org.
Lett. 2003, 5, 4851-4854. (b) Tsunoda, T.; Takagi, H.; Takaba, D.;
Kaku, H.; Ito, S. Tetrahedron Lett. 2000, 41, 235-237. (c) Sabitha, G.;
Reddy, M. M.; Srinivas, D.; Yadav, J. S. Tetrahedron Lett. 1999, 40,
165-166.
8.
For examples, see: Shade, R. E.; Hyde, A. M.; Olsen, J.-C.; Merlic, C.
A. J. Am. Chem. Soc. 2010, 132, 1202-1203. (b) Winternheimer, D. J.;
Merlic, C. A. Org. Lett. 2010, 12, 2508-2510. (c) Wan, Z.; Jones, C. D.;
Koenig, T. M.; Pu, Y. J.; Mitchell, D. Tetrahedron Lett. 2003, 44, 8257-
8259. (d) Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 1381-1384. (e)
Willis, M. C.; Taylor, D.; Gillmore, A. T. Chem. Commun. 2003, 2222-
2223. (f) Okimoto, Y.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2002,
124, 1590-1591.
Scheme 1. Preparation of 6 by means of a Wittig reaction to generate
vinyl ether intermediate 10, followed by hydrogenation.
In summary, we present here a route to the preparation of
various aromatic-functionalized vinyl ethers using a Wittig
approach. Their hydrogenation to the saturated analogs is
streamlined by employing continuous-flow processing.
9.
Edmonds, M.; Abell, A. InModern Carbonyl Olefination, Takeda T.
(Ed), Wiley-VCH, Weinheim, 2003; pp 1-17.
10. (a) Kleinbeck, F.; Carreira, E. M. Angew. Chem. Int. Ed. 2009, 48, 578-
581. (b) Kulkarni, M. G.; Pendharkar, D. S.; Rasne, R. M. Tetrahedron
Lett. 1997, 38, 1459-1462. (c) Paquet, F.; Sinay, P. J. Am. Chem. Soc.
1984, 106, 8313-8315.
11. Earnshaw, C.; Wallis, C. J.; Warren, S. J. Chem. Soc., Perkin Trans. I
1979, 3099-3106.
Acknowledgements
12. See, for example: (a) Rong, Z.-Q.; Zhang, Y.; Chua, R. H. B.; Pan, H.-
J.; Zhao, Y. J. Am. Chem. Soc. 2015, 137, 4944-4947. (b) Ruiz-Olalla,
A.; Würdemann, M. A.; Wanner, M. J.; Ingemann, S.; Van Maarseveen,
J. H.; Hiemstra, H. J. Org. Chem. 2015, 80, 5125-5132. (c) Chepiga, K.
M.; Feng, Y.; Brunelli, N. A.; Jones, C. W.; Davies, H. M. L. Org. Lett.
2013,15, 6136-6139. (d) Lauer, M. G.; Henderson, W. H.; Awad, A.;
Stambuli, J. P. Org. Lett. 2012, 14, 6000-6003. (e) Hellal, M.; Singh, S.;
Cuny, G. D. Tetrahedron 2012, 68, 1674-1681. (f) de la Fuente, M. C.;
Dominguez, D. Tetrahedron 2009, 65, 3653-3658
13. See, for example: (a) Witten, M. R.; Jacobsen, E. N. Org. Lett. 2015,
17, 2772-2775. (b) Kashinath, K.; Jadhav, P. D.; Reddy, D. S. Org.
Biomol. Chem. 2014, 12, 4098-4103. (c) Yamaguchi, S.; Tanaka, H.;
Yamada, R.; Kawauchi, S.; Takahashi, T. Synlett 2012, 23, 1327-1330.
(d) Radi, Marco; Crespan, E.; Falchi, Federico; B., Vincenzo; Z.,
Samantha; M., Fabrizio; S., Silvia; Maga, G.; Botta, M. ChemMedChem
2010, 5, 1226-1231.
We gratefully acknowledge financial support from Faculté des
Sciences, Université de Tunis and the University of Connecticut.
Supplementary Material
Experimental details, characterization of products, and copies
of 1H- and 13C-NMR spectra.
14. Methoxymethyltriphenylphosphonium chloride (1.2 eq.) was dissolved
in anhydrous THF (2 ml/mmol) under an argon atmosphere. The
solution was cooled to -78°C in an acetone/dry ice bath and then BuLi
(1.6M in hexanes, 1.2 eq.) added dropwise. The initially yellow solution
was stirred for 2 h at -78°C and gradually turned dark red. The
aldehyde, (1 eq.) dissolved in anhydrous THF (1 ml/mmol), was added
dropwise and the reaction was stirred for an additional 3 h at -78°C. The
reaction was quenched by the addition of saturated aqueous NaHCO3,
and extracted with ether. The organic layer was separated, dried over
MgSO4, filtered and the solvents were removed on a rotary evaporator.
The crude product was purified by flash column chromatography on
silica gel using a cyclohexane/ethyl acetate mixture as eluent.