Lathanum Trifluoromethanesulfonate [La(OTf)3] Promoted Indium-Mediated Coupling of Ethyl 4-Bromocrotonate with Carbonyl Compounds in Water

Synlett

Volumn 1996, Issue 3, 1996, Pages 263-264

  Diana, Sook Chiang Ho ^a   Sim, Keng Yeow ^a   Loh, Teck Peng ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001089298     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5398     Document Type: Article

References (41)

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9. The allylation reactions of compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191. (b) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910. (c) Petrier, C.; Luche, J.-L.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1449. (d) Einhorn, J., Luche, J.-L. J. Organomet. Chem. 1987, 322, 177. (e) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697. (f) Wilson, S.R.; Guazzaroni, M,E. J. Org. Chem. 1989, 54, 3087. (g) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279. (h) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674. (i) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714. (j) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500; see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem. 1993, 6, 336. (k) Li, C.J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017. (l) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97. (m) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721. (n) Paquette, L.A.; Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863. (o) Wang, R.B.; Lim, C.M.; Tan, C.H.; Lim, B.K.; Sim, K.Y.; Loh, T.P. Tetrahedron Asy. 1995, 6, 1825. (p) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
10. The allylation reactions of compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191. (b) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910. (c) Petrier, C.; Luche, J.-L.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1449. (d) Einhorn, J., Luche, J.-L. J. Organomet. Chem. 1987, 322, 177. (e) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697. (f) Wilson, S.R.; Guazzaroni, M,E. J. Org. Chem. 1989, 54, 3087. (g) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279. (h) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674. (i) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714. (j) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500; see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem. 1993, 6, 336. (k) Li, C.J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017. (l) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97. (m) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721. (n) Paquette, L.A.; Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863. (o) Wang, R.B.; Lim, C.M.; Tan, C.H.; Lim, B.K.; Sim, K.Y.; Loh, T.P. Tetrahedron Asy. 1995, 6, 1825. (p) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
11. The allylation reactions of compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191. (b) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910. (c) Petrier, C.; Luche, J.-L.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1449. (d) Einhorn, J., Luche, J.-L. J. Organomet. Chem. 1987, 322, 177. (e) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697. (f) Wilson, S.R.; Guazzaroni, M,E. J. Org. Chem. 1989, 54, 3087. (g) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279. (h) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674. (i) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714. (j) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500; see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem. 1993, 6, 336. (k) Li, C.J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017. (l) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97. (m) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721. (n) Paquette, L.A.; Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863. (o) Wang, R.B.; Lim, C.M.; Tan, C.H.; Lim, B.K.; Sim, K.Y.; Loh, T.P. Tetrahedron Asy. 1995, 6, 1825. (p) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
12. The allylation reactions of compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191. (b) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910. (c) Petrier, C.; Luche, J.-L.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1449. (d) Einhorn, J., Luche, J.-L. J. Organomet. Chem. 1987, 322, 177. (e) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697. (f) Wilson, S.R.; Guazzaroni, M,E. J. Org. Chem. 1989, 54, 3087. (g) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279. (h) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674. (i) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714. (j) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500; see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem. 1993, 6, 336. (k) Li, C.J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017. (l) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97. (m) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721. (n) Paquette, L.A.; Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863. (o) Wang, R.B.; Lim, C.M.; Tan, C.H.; Lim, B.K.; Sim, K.Y.; Loh, T.P. Tetrahedron Asy. 1995, 6, 1825. (p) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
13. The allylation reactions of compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191. (b) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910. (c) Petrier, C.; Luche, J.-L.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1449. (d) Einhorn, J., Luche, J.-L. J. Organomet. Chem. 1987, 322, 177. (e) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697. (f) Wilson, S.R.; Guazzaroni, M,E. J. Org. Chem. 1989, 54, 3087. (g) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279. (h) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674. (i) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714. (j) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500; see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem. 1993, 6, 336. (k) Li, C.J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017. (l) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97. (m) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721. (n) Paquette, L.A.; Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863. (o) Wang, R.B.; Lim, C.M.; Tan, C.H.; Lim, B.K.; Sim, K.Y.; Loh, T.P. Tetrahedron Asy. 1995, 6, 1825. (p) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
14. The allylation reactions of compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191. (b) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910. (c) Petrier, C.; Luche, J.-L.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1449. (d) Einhorn, J., Luche, J.-L. J. Organomet. Chem. 1987, 322, 177. (e) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697. (f) Wilson, S.R.; Guazzaroni, M,E. J. Org. Chem. 1989, 54, 3087. (g) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279. (h) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674. (i) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714. (j) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500; see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem. 1993, 6, 336. (k) Li, C.J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017. (l) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97. (m) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721. (n) Paquette, L.A.; Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863. (o) Wang, R.B.; Lim, C.M.; Tan, C.H.; Lim, B.K.; Sim, K.Y.; Loh, T.P. Tetrahedron Asy. 1995, 6, 1825. (p) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
15. The allylation reactions of compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191. (b) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910. (c) Petrier, C.; Luche, J.-L.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1449. (d) Einhorn, J., Luche, J.-L. J. Organomet. Chem. 1987, 322, 177. (e) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697. (f) Wilson, S.R.; Guazzaroni, M,E. J. Org. Chem. 1989, 54, 3087. (g) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279. (h) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674. (i) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714. (j) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500; see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem. 1993, 6, 336. (k) Li, C.J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017. (l) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97. (m) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721. (n) Paquette, L.A.; Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863. (o) Wang, R.B.; Lim, C.M.; Tan, C.H.; Lim, B.K.; Sim, K.Y.; Loh, T.P. Tetrahedron Asy. 1995, 6, 1825. (p) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
16. The allylation reactions of compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191. (b) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910. (c) Petrier, C.; Luche, J.-L.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1449. (d) Einhorn, J., Luche, J.-L. J. Organomet. Chem. 1987, 322, 177. (e) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697. (f) Wilson, S.R.; Guazzaroni, M,E. J. Org. Chem. 1989, 54, 3087. (g) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279. (h) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674. (i) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714. (j) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500; see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem. 1993, 6, 336. (k) Li, C.J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017. (l) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97. (m) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721. (n) Paquette, L.A.; Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863. (o) Wang, R.B.; Lim, C.M.; Tan, C.H.; Lim, B.K.; Sim, K.Y.; Loh, T.P. Tetrahedron Asy. 1995, 6, 1825. (p) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
17. The allylation reactions of compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191. (b) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910. (c) Petrier, C.; Luche, J.-L.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1449. (d) Einhorn, J., Luche, J.-L. J. Organomet. Chem. 1987, 322, 177. (e) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697. (f) Wilson, S.R.; Guazzaroni, M,E. J. Org. Chem. 1989, 54, 3087. (g) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279. (h) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674. (i) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714. (j) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500; see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem. 1993, 6, 336. (k) Li, C.J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017. (l) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97. (m) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721. (n) Paquette, L.A.; Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863. (o) Wang, R.B.; Lim, C.M.; Tan, C.H.; Lim, B.K.; Sim, K.Y.; Loh, T.P. Tetrahedron Asy. 1995, 6, 1825. (p) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
18. The allylation reactions of compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191. (b) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910. (c) Petrier, C.; Luche, J.-L.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1449. (d) Einhorn, J., Luche, J.-L. J. Organomet. Chem. 1987, 322, 177. (e) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697. (f) Wilson, S.R.; Guazzaroni, M,E. J. Org. Chem. 1989, 54, 3087. (g) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279. (h) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674. (i) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714. (j) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500; see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem. 1993, 6, 336. (k) Li, C.J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017. (l) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97. (m) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721. (n) Paquette, L.A.; Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863. (o) Wang, R.B.; Lim, C.M.; Tan, C.H.; Lim, B.K.; Sim, K.Y.; Loh, T.P. Tetrahedron Asy. 1995, 6, 1825. (p) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
19. The allylation reactions of compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191. (b) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910. (c) Petrier, C.; Luche, J.-L.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1449. (d) Einhorn, J., Luche, J.-L. J. Organomet. Chem. 1987, 322, 177. (e) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697. (f) Wilson, S.R.; Guazzaroni, M,E. J. Org. Chem. 1989, 54, 3087. (g) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279. (h) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674. (i) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714. (j) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500; see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem. 1993, 6, 336. (k) Li, C.J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017. (l) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97. (m) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721. (n) Paquette, L.A.; Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863. (o) Wang, R.B.; Lim, C.M.; Tan, C.H.; Lim, B.K.; Sim, K.Y.; Loh, T.P. Tetrahedron Asy. 1995, 6, 1825. (p) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
20. The allylation reactions of compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191. (b) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910. (c) Petrier, C.; Luche, J.-L.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1449. (d) Einhorn, J., Luche, J.-L. J. Organomet. Chem. 1987, 322, 177. (e) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697. (f) Wilson, S.R.; Guazzaroni, M,E. J. Org. Chem. 1989, 54, 3087. (g) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279. (h) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674. (i) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714. (j) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500; see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem. 1993, 6, 336. (k) Li, C.J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017. (l) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97. (m) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721. (n) Paquette, L.A.; Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863. (o) Wang, R.B.; Lim, C.M.; Tan, C.H.; Lim, B.K.; Sim, K.Y.; Loh, T.P. Tetrahedron Asy. 1995, 6, 1825. (p) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
21. The allylation reactions of compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191. (b) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910. (c) Petrier, C.; Luche, J.-L.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1449. (d) Einhorn, J., Luche, J.-L. J. Organomet. Chem. 1987, 322, 177. (e) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697. (f) Wilson, S.R.; Guazzaroni, M,E. J. Org. Chem. 1989, 54, 3087. (g) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279. (h) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674. (i) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714. (j) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500; see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem. 1993, 6, 336. (k) Li, C.J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017. (l) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97. (m) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721. (n) Paquette, L.A.; Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863. (o) Wang, R.B.; Lim, C.M.; Tan, C.H.; Lim, B.K.; Sim, K.Y.; Loh, T.P. Tetrahedron Asy. 1995, 6, 1825. (p) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
22. The allylation reactions of compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191. (b) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910. (c) Petrier, C.; Luche, J.-L.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1449. (d) Einhorn, J., Luche, J.-L. J. Organomet. Chem. 1987, 322, 177. (e) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697. (f) Wilson, S.R.; Guazzaroni, M,E. J. Org. Chem. 1989, 54, 3087. (g) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279. (h) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674. (i) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714. (j) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500; see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem. 1993, 6, 336. (k) Li, C.J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017. (l) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97. (m) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721. (n) Paquette, L.A.; Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863. (o) Wang, R.B.; Lim, C.M.; Tan, C.H.; Lim, B.K.; Sim, K.Y.; Loh, T.P. Tetrahedron Asy. 1995, 6, 1825. (p) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
23. The allylation reactions of compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191. (b) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910. (c) Petrier, C.; Luche, J.-L.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1449. (d) Einhorn, J., Luche, J.-L. J. Organomet. Chem. 1987, 322, 177. (e) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697. (f) Wilson, S.R.; Guazzaroni, M,E. J. Org. Chem. 1989, 54, 3087. (g) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279. (h) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674. (i) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714. (j) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500; see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem. 1993, 6, 336. (k) Li, C.J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017. (l) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97. (m) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721. (n) Paquette, L.A.; Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863. (o) Wang, R.B.; Lim, C.M.; Tan, C.H.; Lim, B.K.; Sim, K.Y.; Loh, T.P. Tetrahedron Asy. 1995, 6, 1825. (p) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
24. The allylation reactions of compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191. (b) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910. (c) Petrier, C.; Luche, J.-L.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1449. (d) Einhorn, J., Luche, J.-L. J. Organomet. Chem. 1987, 322, 177. (e) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697. (f) Wilson, S.R.; Guazzaroni, M,E. J. Org. Chem. 1989, 54, 3087. (g) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279. (h) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674. (i) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714. (j) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500; see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem. 1993, 6, 336. (k) Li, C.J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017. (l) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97. (m) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721. (n) Paquette, L.A.; Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863. (o) Wang, R.B.; Lim, C.M.; Tan, C.H.; Lim, B.K.; Sim, K.Y.; Loh, T.P. Tetrahedron Asy. 1995, 6, 1825. (p) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
25. The allylation reactions of compounds using allyl halides and Zn, Sn, or In in aqueous media were previously reported. (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191. (b) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910. (c) Petrier, C.; Luche, J.-L.; Einhorn, J. Tetrahedron Lett. 1985, 26, 1449. (d) Einhorn, J., Luche, J.-L. J. Organomet. Chem. 1987, 322, 177. (e) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697. (f) Wilson, S.R.; Guazzaroni, M,E. J. Org. Chem. 1989, 54, 3087. (g) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279. (h) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674. (i) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714. (j) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500; see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem. 1993, 6, 336. (k) Li, C.J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017. (l) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97. (m) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721. (n) Paquette, L.A.; Mitzel, T.M. Tetrahedron Lett. 1995, 36, 6863. (o) Wang, R.B.; Lim, C.M.; Tan, C.H.; Lim, B.K.; Sim, K.Y.; Loh, T.P. Tetrahedron Asy. 1995, 6, 1825. (p) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
26. Reviews on organic reactions in aqueous media: (a) Li, C.J. Chem. Rev. 1993, 93, 2023. (b) Kobayashi, S.; Hachiya, I.; Takahori, T. Synthesis 1993, 371. (c) Pardo, R.; Santelli, M. Bull. Chem. Soc. Fr. 1985, 99. (d) Ressig, H.-U. In Organic Synthesis Highlights; VCH: Weinheim, 1991; p71. (e) Einhorn, C.; Einhorn, J.; Luche, J.-L. Synthesis 1989, 787.
27. Reviews on organic reactions in aqueous media: (a) Li, C.J. Chem. Rev. 1993, 93, 2023. (b) Kobayashi, S.; Hachiya, I.; Takahori, T. Synthesis 1993, 371. (c) Pardo, R.; Santelli, M. Bull. Chem. Soc. Fr. 1985, 99. (d) Ressig, H.-U. In Organic Synthesis Highlights; VCH: Weinheim, 1991; p71. (e) Einhorn, C.; Einhorn, J.; Luche, J.-L. Synthesis 1989, 787.
28. Reviews on organic reactions in aqueous media: (a) Li, C.J. Chem. Rev. 1993, 93, 2023. (b) Kobayashi, S.; Hachiya, I.; Takahori, T. Synthesis 1993, 371. (c) Pardo, R.; Santelli, M. Bull. Chem. Soc. Fr. 1985, 99. (d) Ressig, H.-U. In Organic Synthesis Highlights; VCH: Weinheim, 1991; p71. (e) Einhorn, C.; Einhorn, J.; Luche, J.-L. Synthesis 1989, 787.
29. Reviews on organic reactions in aqueous media: (a) Li, C.J. Chem. Rev. 1993, 93, 2023. (b) Kobayashi, S.; Hachiya, I.; Takahori, T. Synthesis 1993, 371. (c) Pardo, R.; Santelli, M. Bull. Chem. Soc. Fr. 1985, 99. (d) Ressig, H.-U. In Organic Synthesis Highlights; VCH: Weinheim, 1991; p71. (e) Einhorn, C.; Einhorn, J.; Luche, J.-L. Synthesis 1989, 787.
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41. This research was assisted financially by the National University of Singapore (RP 930657, RP 940633, RP 950609).