One-pot, three-component synthesis of linearly substituted homoallylic alcohols via allyl(isopropoxy)dimethylsilane

Organic Letters

Volumn 6, Issue 18, 2004, Pages 3091-3094

  Li, Lianhai ^a   Navasero, Neenah ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALLYL COMPOUND; CARBONYL DERIVATIVE; PALLADIUM; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; LINEAR SYSTEM; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

ALCOHOLS; ALLYL COMPOUNDS; CATALYSIS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; SILANES; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 4544268096     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048892l     Document Type: Article

References (66)

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25. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
26. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
27. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
28. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
29. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
30. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
31. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
32. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
33. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
34. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
35. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
36. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
37. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
38. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
39. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
40. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
41. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
42. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
43. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
44. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
45. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
46. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
47. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
48. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
49. (I) Wittig: (a) Boesen, T.; Feeder, N.; Eastgate, M. D.; Fox, D. J.; Medlock, J. A.; Tyzack, C. R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 118. (b) Enholm, E. J.; Satici, H.; Prasad, G. J. Org. Chem. 1990, 55, 324. (c) Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Cheik-Rouhou, F. Synth. Commun. 1986, 16, 1617. (d) Maryanoff, B. E.; Reitz, A. B.; Duhl-Emswiler, B. A. J. Am. Chem. Soc. 1985, 107, 217. (e) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025. (f) Hands, A. R.; Mercer, A. J. H. J. Chem. Soc. C 1968, 2448. (II) Addition to carbonyls: see examples and references in (a) Lautens, M.; Maddess, M. L.; Sauer, E. L.; Quellet, S. G. Org. Lett. 2002, 4, 83. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079. (c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (e) Hayashi, T.; Kumada, M. J. Org. Chem. 1983, 48, 281. (f) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991. (g) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetrahedron Lett. 2001, 42, 8701. (III) Ene-reaction: (a) Salomon, M. F.; Pardo, S. M.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797. (b) Gill, G. B.; Hj Idris, M. S. Tetrahedron 1993, 49, 219. (c) Beak, P.; Song, Z.; Resek, J. E. J. Org. Chem. 1992, 57, 944. (IV) Allyl transfer: (a) Loh, T. P.; Tan, K. T.; Hu, Q. Y. Angew. Chem., Int. Ed. 2001, 40, 2921. (b) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609. (V) Cross-metathesis: Barrett, A. G. M.; Beall, J. C.; Gibson, V. C.; Giles, M. R.; Walker, G. L. P. Chem. Commun. 1996, 2229. (VI) Cross-coupling: Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. 1998, 37, 2534. (VII) Heck reaction: Dyker, G.; Markwitz, H. Synthesis 1998, 1750. (VIII) Miscellaneous synthesis: (a) Trost, B. M.; Quayle, P. J. Am. Chem. Soc. 1984, 106, 2469. Gupta, A.; Vankar, Y. D. Tetrahedron Lett. 1999, 40, 1369. (b) Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Tetrahedron 1995, 51, 9873. (c) Maleczka, R. E.; Geng, F. Org. Lett. 1999, 1, 1111.
50. Hirashita, T.; Yamamura, H.; Kawai, M.; Araki. S. Chem. Commun. 2001, 387.
51. Shimizu, M.; Kitagawa, H.; Kurahashi, T.; Hiyama, T. Angew. Chem., Int. Ed. 2001, 40, 4283.
52. Denmark, S. E.; Yang, S. M. Org. Lett. 2001, 3, 1749.
53. Examples of γ-addition of various silylallylmetals to carbonyl compounds: (a) Corriu, R. J. P.; Guerin, C.; M'Boula, J. Tetrahedron Lett. 1981, 22, 2985. (b) Ehlinger, E.; Magnus, P. J. Am. Chem. Soc. 1980, 102, 5004. (c) Chan, T. H.; Labrecque, D. Tetrahedron Lett. 1992, 33, 7997.
54. Examples of γ-addition of various silylallylmetals to carbonyl compounds: (a) Corriu, R. J. P.; Guerin, C.; M'Boula, J. Tetrahedron Lett. 1981, 22, 2985. (b) Ehlinger, E.; Magnus, P. J. Am. Chem. Soc. 1980, 102, 5004. (c) Chan, T. H.; Labrecque, D. Tetrahedron Lett. 1992, 33, 7997.
55. Examples of γ-addition of various silylallylmetals to carbonyl compounds: (a) Corriu, R. J. P.; Guerin, C.; M'Boula, J. Tetrahedron Lett. 1981, 22, 2985. (b) Ehlinger, E.; Magnus, P. J. Am. Chem. Soc. 1980, 102, 5004. (c) Chan, T. H.; Labrecque, D. Tetrahedron Lett. 1992, 33, 7997.
56. (d) Liu, L.; Wang, D. J. Chem. Res., Synop. 1998, 612.
57. Tamao, K.; Nakajo, E.; Ito, Y. Synth. Commun. 1987, 17, 1637.
58. Schlosser, M.; Franzini, L. Synthesis 1998, 707.
59. Various reaction temperatures and reaction times were tested; no better yield of 7 was obtained.
60. By using 3% and 4% of the catalyst, 1a was obtained in 89% and 95% yield, respectively.
61. Literature example of Pd-catalyzed homocoupling in the presence Bu
62. Low yield seemed caused by instability of 1g under the conditions.
63. E and Z ratio about 6:1 of 2-bromostyrene was reflected in 1h accordingly.
64. This amount was used to match the yield of vinylsilane 7; the product yields were calculated on the basis of the limiting reagent aryl iodides used.
65. No attempt was done to optimize the reaction time.
66. Conditions were not modified for different carbonyl compounds.