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Volumn 44, Issue 5, 2003, Pages 911-914

Indium-mediated allylation of carbonyl compounds with an allylic bromide in aqueous media: Anomalous syn-diastereoselectivity regardless of allylic bromide geometry

Author keywords

[No Author keywords available]

Indexed keywords

BROMIDE; CARBONYL DERIVATIVE; INDIUM;

EID: 0037467855     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02773-9     Document Type: Article
Times cited : (35)

References (32)
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    • For the pioneering work on the indium-mediated allylation reaction of carbonyl compounds: (a) Li, C. J. Chem. Rev. 1993, 93, 2023; (b) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181; (c) Cintas, P. Synlett. 1995, 1087; (d) Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228; (e) Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228; (f) Araki, S.; Ito, H. J. Org. Chem. 1988, 53, 1831; (g) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917; (h) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931; (i) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318; (j) Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1997, 62, 4293; (k) Isaac, M. B.; Paquette, L. A. J. Org. Chem. 1997, 62, 5333; (l) Hirashita, T.; Kamei, T. J. Org. Chem. 1999, 64, 172; (m) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217.
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    • For the pioneering work on the indium-mediated allylation reaction of carbonyl compounds: (a) Li, C. J. Chem. Rev. 1993, 93, 2023; (b) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181; (c) Cintas, P. Synlett. 1995, 1087; (d) Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228; (e) Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228; (f) Araki, S.; Ito, H. J. Org. Chem. 1988, 53, 1831; (g) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917; (h) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931; (i) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318; (j) Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1997, 62, 4293; (k) Isaac, M. B.; Paquette, L. A. J. Org. Chem. 1997, 62, 5333; (l) Hirashita, T.; Kamei, T. J. Org. Chem. 1999, 64, 172; (m) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217.
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    • For the pioneering work on the indium-mediated allylation reaction of carbonyl compounds: (a) Li, C. J. Chem. Rev. 1993, 93, 2023; (b) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181; (c) Cintas, P. Synlett. 1995, 1087; (d) Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228; (e) Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228; (f) Araki, S.; Ito, H. J. Org. Chem. 1988, 53, 1831; (g) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917; (h) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931; (i) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318; (j) Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1997, 62, 4293; (k) Isaac, M. B.; Paquette, L. A. J. Org. Chem. 1997, 62, 5333; (l) Hirashita, T.; Kamei, T. J. Org. Chem. 1999, 64, 172; (m) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217.
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    • For the pioneering work on the indium-mediated allylation reaction of carbonyl compounds: (a) Li, C. J. Chem. Rev. 1993, 93, 2023; (b) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181; (c) Cintas, P. Synlett. 1995, 1087; (d) Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228; (e) Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228; (f) Araki, S.; Ito, H. J. Org. Chem. 1988, 53, 1831; (g) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917; (h) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931; (i) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318; (j) Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1997, 62, 4293; (k) Isaac, M. B.; Paquette, L. A. J. Org. Chem. 1997, 62, 5333; (l) Hirashita, T.; Kamei, T. J. Org. Chem. 1999, 64, 172; (m) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217.
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    • For the pioneering work on the indium-mediated allylation reaction of carbonyl compounds: (a) Li, C. J. Chem. Rev. 1993, 93, 2023; (b) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181; (c) Cintas, P. Synlett. 1995, 1087; (d) Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228; (e) Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228; (f) Araki, S.; Ito, H. J. Org. Chem. 1988, 53, 1831; (g) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917; (h) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931; (i) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318; (j) Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1997, 62, 4293; (k) Isaac, M. B.; Paquette, L. A. J. Org. Chem. 1997, 62, 5333; (l) Hirashita, T.; Kamei, T. J. Org. Chem. 1999, 64, 172; (m) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217.
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    • Paquette, L.A.1    Mitzel, T.M.2
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    • For the pioneering work on the indium-mediated allylation reaction of carbonyl compounds: (a) Li, C. J. Chem. Rev. 1993, 93, 2023; (b) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181; (c) Cintas, P. Synlett. 1995, 1087; (d) Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228; (e) Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228; (f) Araki, S.; Ito, H. J. Org. Chem. 1988, 53, 1831; (g) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917; (h) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931; (i) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318; (j) Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1997, 62, 4293; (k) Isaac, M. B.; Paquette, L. A. J. Org. Chem. 1997, 62, 5333; (l) Hirashita, T.; Kamei, T. J. Org. Chem. 1999, 64, 172; (m) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217.
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    • Isaac, M.B.1    Paquette, L.A.2
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    • For the pioneering work on the indium-mediated allylation reaction of carbonyl compounds: (a) Li, C. J. Chem. Rev. 1993, 93, 2023; (b) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181; (c) Cintas, P. Synlett. 1995, 1087; (d) Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228; (e) Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228; (f) Araki, S.; Ito, H. J. Org. Chem. 1988, 53, 1831; (g) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917; (h) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931; (i) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318; (j) Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1997, 62, 4293; (k) Isaac, M. B.; Paquette, L. A. J. Org. Chem. 1997, 62, 5333; (l) Hirashita, T.; Kamei, T. J. Org. Chem. 1999, 64, 172; (m) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217.
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    • For the pioneering work on the indium-mediated allylation reaction of carbonyl compounds: (a) Li, C. J. Chem. Rev. 1993, 93, 2023; (b) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181; (c) Cintas, P. Synlett. 1995, 1087; (d) Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228; (e) Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228; (f) Araki, S.; Ito, H. J. Org. Chem. 1988, 53, 1831; (g) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917; (h) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931; (i) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318; (j) Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1997, 62, 4293; (k) Isaac, M. B.; Paquette, L. A. J. Org. Chem. 1997, 62, 5333; (l) Hirashita, T.; Kamei, T. J. Org. Chem. 1999, 64, 172; (m) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217.
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    • Lanthanide triflate has been shown to increase the rate and selectivity of the indium-mediated allylation reaction of carbonyl compounds: (a) Wang, R. B.; Lim, B. K., Sim K. Y.; Loh, T. P. Tetrahedron: Asymmetry 1995, 6, 1825; (b) Ho, D. S.-C.; Sim, K. Y.; Loh, T. P. Synlett. 1996, 3, 263; (c) Loh, T. P.; Wang, R. B.; Tan, K. L.; Sim, K. Y. Main Group Metal Chemistry, 1997, 20, 237; (d) Loh, T. P.; Cao, G. Q.; Pei, J. Tetrahedron Lett. 1998, 39, 1453.
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    • Lanthanide triflate has been shown to increase the rate and selectivity of the indium-mediated allylation reaction of carbonyl compounds: (a) Wang, R. B.; Lim, B. K., Sim K. Y.; Loh, T. P. Tetrahedron: Asymmetry 1995, 6, 1825; (b) Ho, D. S.-C.; Sim, K. Y.; Loh, T. P. Synlett. 1996, 3, 263; (c) Loh, T. P.; Wang, R. B.; Tan, K. L.; Sim, K. Y. Main Group Metal Chemistry, 1997, 20, 237; (d) Loh, T. P.; Cao, G. Q.; Pei, J. Tetrahedron Lett. 1998, 39, 1453.
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    • Lanthanide triflate has been shown to increase the rate and selectivity of the indium-mediated allylation reaction of carbonyl compounds: (a) Wang, R. B.; Lim, B. K., Sim K. Y.; Loh, T. P. Tetrahedron: Asymmetry 1995, 6, 1825; (b) Ho, D. S.-C.; Sim, K. Y.; Loh, T. P. Synlett. 1996, 3, 263; (c) Loh, T. P.; Wang, R. B.; Tan, K. L.; Sim, K. Y. Main Group Metal Chemistry, 1997, 20, 237; (d) Loh, T. P.; Cao, G. Q.; Pei, J. Tetrahedron Lett. 1998, 39, 1453.
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    • Lanthanide triflate has been shown to increase the rate and selectivity of the indium-mediated allylation reaction of carbonyl compounds: (a) Wang, R. B.; Lim, B. K., Sim K. Y.; Loh, T. P. Tetrahedron: Asymmetry 1995, 6, 1825; (b) Ho, D. S.-C.; Sim, K. Y.; Loh, T. P. Synlett. 1996, 3, 263; (c) Loh, T. P.; Wang, R. B.; Tan, K. L.; Sim, K. Y. Main Group Metal Chemistry, 1997, 20, 237; (d) Loh, T. P.; Cao, G. Q.; Pei, J. Tetrahedron Lett. 1998, 39, 1453.
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    • 4, concentrated under vacuum, and purified by flash column chromatography to afford the homoallylic alcohol.
    • 4, concentrated under vacuum, and purified by flash column chromatography to afford the homoallylic alcohol.


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