Synthesis of (E)- and (Z)-alkenylphosphonates using vinylboronates

Organic Letters

Volumn 5, Issue 5, 2003, Pages 729-731

  Kabalka, George W ^a   Guchhait, Sankar K ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; BORONIC ACID DERIVATIVE; ESTER DERIVATIVE; HALOGEN; NITROGEN; ORGANOPHOSPHATE; PHOSPHONIC ACID DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; MICHAEL ADDITION; PINACOL REARRANGEMENT; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0042188362     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027515a     Document Type: Article

References (46)

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13. For reviews, see: Minami, T.; Motoyoshiya, J. Synthesis 1992, 333. (a) Enders, D.; Wahl, H.; Papadopoulos, K. Tetrahedron 1997, 53, 12961. (b) Cristau, H.-J.; Pirat, J.-L.; Drag, M.; Kafarski, P. Tetrahedron Lett. 2000, 41, 9781. (c) Yokomatsu, T.; Yamagishi, T.; Suemune, K.; Yoshida, Y.; Shibuya, S. Tetrahedron 1998, 54, 767. (d) Kim, D. Y.; Rhie, D. Y. Tetrahedron 1997, 53, 13603. (e) Cristau, H.-J.; Mbianda, X. Y.; Geze, A.; Beziat, Y.; Gasc, M. B. J. Organomet. Chem. 1998, 571, 189. (f) Junker, H.-D.; Fessner, W.-D. Tetrahedron Lett. 1998, 39, 269. (g) Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83. (h) Ranu, B. C.; Guchhait, S. K.; Ghosh, K. J. Org. Chem. 1998, 63, 5250.
14. For reviews, see: Minami, T.; Motoyoshiya, J. Synthesis 1992, 333. (a) Enders, D.; Wahl, H.; Papadopoulos, K. Tetrahedron 1997, 53, 12961. (b) Cristau, H.-J.; Pirat, J.-L.; Drag, M.; Kafarski, P. Tetrahedron Lett. 2000, 41, 9781. (c) Yokomatsu, T.; Yamagishi, T.; Suemune, K.; Yoshida, Y.; Shibuya, S. Tetrahedron 1998, 54, 767. (d) Kim, D. Y.; Rhie, D. Y. Tetrahedron 1997, 53, 13603. (e) Cristau, H.-J.; Mbianda, X. Y.; Geze, A.; Beziat, Y.; Gasc, M. B. J. Organomet. Chem. 1998, 571, 189. (f) Junker, H.-D.; Fessner, W.-D. Tetrahedron Lett. 1998, 39, 269. (g) Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83. (h) Ranu, B. C.; Guchhait, S. K.; Ghosh, K. J. Org. Chem. 1998, 63, 5250.
15. For reviews, see: Minami, T.; Motoyoshiya, J. Synthesis 1992, 333. (a) Enders, D.; Wahl, H.; Papadopoulos, K. Tetrahedron 1997, 53, 12961. (b) Cristau, H.-J.; Pirat, J.-L.; Drag, M.; Kafarski, P. Tetrahedron Lett. 2000, 41, 9781. (c) Yokomatsu, T.; Yamagishi, T.; Suemune, K.; Yoshida, Y.; Shibuya, S. Tetrahedron 1998, 54, 767. (d) Kim, D. Y.; Rhie, D. Y. Tetrahedron 1997, 53, 13603. (e) Cristau, H.-J.; Mbianda, X. Y.; Geze, A.; Beziat, Y.; Gasc, M. B. J. Organomet. Chem. 1998, 571, 189. (f) Junker, H.-D.; Fessner, W.-D. Tetrahedron Lett. 1998, 39, 269. (g) Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83. (h) Ranu, B. C.; Guchhait, S. K.; Ghosh, K. J. Org. Chem. 1998, 63, 5250.
16. For reviews, see: Minami, T.; Motoyoshiya, J. Synthesis 1992, 333. (a) Enders, D.; Wahl, H.; Papadopoulos, K. Tetrahedron 1997, 53, 12961. (b) Cristau, H.-J.; Pirat, J.-L.; Drag, M.; Kafarski, P. Tetrahedron Lett. 2000, 41, 9781. (c) Yokomatsu, T.; Yamagishi, T.; Suemune, K.; Yoshida, Y.; Shibuya, S. Tetrahedron 1998, 54, 767. (d) Kim, D. Y.; Rhie, D. Y. Tetrahedron 1997, 53, 13603. (e) Cristau, H.-J.; Mbianda, X. Y.; Geze, A.; Beziat, Y.; Gasc, M. B. J. Organomet. Chem. 1998, 571, 189. (f) Junker, H.-D.; Fessner, W.-D. Tetrahedron Lett. 1998, 39, 269. (g) Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83. (h) Ranu, B. C.; Guchhait, S. K.; Ghosh, K. J. Org. Chem. 1998, 63, 5250.
17. For reviews, see: Minami, T.; Motoyoshiya, J. Synthesis 1992, 333. (a) Enders, D.; Wahl, H.; Papadopoulos, K. Tetrahedron 1997, 53, 12961. (b) Cristau, H.-J.; Pirat, J.-L.; Drag, M.; Kafarski, P. Tetrahedron Lett. 2000, 41, 9781. (c) Yokomatsu, T.; Yamagishi, T.; Suemune, K.; Yoshida, Y.; Shibuya, S. Tetrahedron 1998, 54, 767. (d) Kim, D. Y.; Rhie, D. Y. Tetrahedron 1997, 53, 13603. (e) Cristau, H.-J.; Mbianda, X. Y.; Geze, A.; Beziat, Y.; Gasc, M. B. J. Organomet. Chem. 1998, 571, 189. (f) Junker, H.-D.; Fessner, W.-D. Tetrahedron Lett. 1998, 39, 269. (g) Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83. (h) Ranu, B. C.; Guchhait, S. K.; Ghosh, K. J. Org. Chem. 1998, 63, 5250.
18. For reviews, see: Minami, T.; Motoyoshiya, J. Synthesis 1992, 333. (a) Enders, D.; Wahl, H.; Papadopoulos, K. Tetrahedron 1997, 53, 12961. (b) Cristau, H.-J.; Pirat, J.-L.; Drag, M.; Kafarski, P. Tetrahedron Lett. 2000, 41, 9781. (c) Yokomatsu, T.; Yamagishi, T.; Suemune, K.; Yoshida, Y.; Shibuya, S. Tetrahedron 1998, 54, 767. (d) Kim, D. Y.; Rhie, D. Y. Tetrahedron 1997, 53, 13603. (e) Cristau, H.-J.; Mbianda, X. Y.; Geze, A.; Beziat, Y.; Gasc, M. B. J. Organomet. Chem. 1998, 571, 189. (f) Junker, H.-D.; Fessner, W.-D. Tetrahedron Lett. 1998, 39, 269. (g) Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83. (h) Ranu, B. C.; Guchhait, S. K.; Ghosh, K. J. Org. Chem. 1998, 63, 5250.
19. For reviews, see: Minami, T.; Motoyoshiya, J. Synthesis 1992, 333. (a) Enders, D.; Wahl, H.; Papadopoulos, K. Tetrahedron 1997, 53, 12961. (b) Cristau, H.-J.; Pirat, J.-L.; Drag, M.; Kafarski, P. Tetrahedron Lett. 2000, 41, 9781. (c) Yokomatsu, T.; Yamagishi, T.; Suemune, K.; Yoshida, Y.; Shibuya, S. Tetrahedron 1998, 54, 767. (d) Kim, D. Y.; Rhie, D. Y. Tetrahedron 1997, 53, 13603. (e) Cristau, H.-J.; Mbianda, X. Y.; Geze, A.; Beziat, Y.; Gasc, M. B. J. Organomet. Chem. 1998, 571, 189. (f) Junker, H.-D.; Fessner, W.-D. Tetrahedron Lett. 1998, 39, 269. (g) Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83. (h) Ranu, B. C.; Guchhait, S. K.; Ghosh, K. J. Org. Chem. 1998, 63, 5250.
20. Hydrophosphorylation of terminal alkynes: (a) Zhao, C.-Q.; Han, L. B.; Goto, M.; Tanaka, M. Angew Chem., Int. Ed. 2001, 40, 1929. (b) Han, L. B. Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. Zirconation of alkynylphosphonates: (c) Quntar, A. A. A.; Melman, A.; Srebnik, M. J. Org. Chem. 2002, 67, 3769. Carbocupration: (d) Gil, J. M.; Oh, D. Y. J. Org. Chem. 1999, 64, 2950. Catalytic hydrogenation of alkynylphosphonates (e) Cristau, H.-J.; Mbianda, X. Y.; Beziat, Y.; Gasc, M. B. J. Organomet. Chem. 1997, 529, 301. Radical trapping: (f) Jiao, X.-Y.; Bentrude, W. G. J. Am. Chem. Soc. 1999, 121, 6088. Allylic rearrangement: (g) Muthiah, C.; Kumar, K. P.; Mani, C. A.; Swamy, K. C. K. J. Org. Chem. 2000, 65, 3733. Triflation: (h) Okauchi, T.; Yano, T.; Fukamachi, T.; Ichikawa, J.; Minami, T. Tetrahedron Lett. 1999, 40, 5337. Wittig: (i) Xu, Y.; Flavin, M. T.; Xu, Z. Q. J. Org. Chem. 1996, 61, 7697. Peterson olefination: (j) Washbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1996, 52, 14199.
21. Hydrophosphorylation of terminal alkynes: (a) Zhao, C.-Q.; Han, L. B.; Goto, M.; Tanaka, M. Angew Chem., Int. Ed. 2001, 40, 1929. (b) Han, L. B. Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. Zirconation of alkynylphosphonates: (c) Quntar, A. A. A.; Melman, A.; Srebnik, M. J. Org. Chem. 2002, 67, 3769. Carbocupration: (d) Gil, J. M.; Oh, D. Y. J. Org. Chem. 1999, 64, 2950. Catalytic hydrogenation of alkynylphosphonates (e) Cristau, H.-J.; Mbianda, X. Y.; Beziat, Y.; Gasc, M. B. J. Organomet. Chem. 1997, 529, 301. Radical trapping: (f) Jiao, X.-Y.; Bentrude, W. G. J. Am. Chem. Soc. 1999, 121, 6088. Allylic rearrangement: (g) Muthiah, C.; Kumar, K. P.; Mani, C. A.; Swamy, K. C. K. J. Org. Chem. 2000, 65, 3733. Triflation: (h) Okauchi, T.; Yano, T.; Fukamachi, T.; Ichikawa, J.; Minami, T. Tetrahedron Lett. 1999, 40, 5337. Wittig: (i) Xu, Y.; Flavin, M. T.; Xu, Z. Q. J. Org. Chem. 1996, 61, 7697. Peterson olefination: (j) Washbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1996, 52, 14199.
22. Hydrophosphorylation of terminal alkynes: (a) Zhao, C.-Q.; Han, L. B.; Goto, M.; Tanaka, M. Angew Chem., Int. Ed. 2001, 40, 1929. (b) Han, L. B. Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. Zirconation of alkynylphosphonates: (c) Quntar, A. A. A.; Melman, A.; Srebnik, M. J. Org. Chem. 2002, 67, 3769. Carbocupration: (d) Gil, J. M.; Oh, D. Y. J. Org. Chem. 1999, 64, 2950. Catalytic hydrogenation of alkynylphosphonates (e) Cristau, H.-J.; Mbianda, X. Y.; Beziat, Y.; Gasc, M. B. J. Organomet. Chem. 1997, 529, 301. Radical trapping: (f) Jiao, X.-Y.; Bentrude, W. G. J. Am. Chem. Soc. 1999, 121, 6088. Allylic rearrangement: (g) Muthiah, C.; Kumar, K. P.; Mani, C. A.; Swamy, K. C. K. J. Org. Chem. 2000, 65, 3733. Triflation: (h) Okauchi, T.; Yano, T.; Fukamachi, T.; Ichikawa, J.; Minami, T. Tetrahedron Lett. 1999, 40, 5337. Wittig: (i) Xu, Y.; Flavin, M. T.; Xu, Z. Q. J. Org. Chem. 1996, 61, 7697. Peterson olefination: (j) Washbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1996, 52, 14199.
23. Hydrophosphorylation of terminal alkynes: (a) Zhao, C.-Q.; Han, L. B.; Goto, M.; Tanaka, M. Angew Chem., Int. Ed. 2001, 40, 1929. (b) Han, L. B. Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. Zirconation of alkynylphosphonates: (c) Quntar, A. A. A.; Melman, A.; Srebnik, M. J. Org. Chem. 2002, 67, 3769. Carbocupration: (d) Gil, J. M.; Oh, D. Y. J. Org. Chem. 1999, 64, 2950. Catalytic hydrogenation of alkynylphosphonates (e) Cristau, H.-J.; Mbianda, X. Y.; Beziat, Y.; Gasc, M. B. J. Organomet. Chem. 1997, 529, 301. Radical trapping: (f) Jiao, X.-Y.; Bentrude, W. G. J. Am. Chem. Soc. 1999, 121, 6088. Allylic rearrangement: (g) Muthiah, C.; Kumar, K. P.; Mani, C. A.; Swamy, K. C. K. J. Org. Chem. 2000, 65, 3733. Triflation: (h) Okauchi, T.; Yano, T.; Fukamachi, T.; Ichikawa, J.; Minami, T. Tetrahedron Lett. 1999, 40, 5337. Wittig: (i) Xu, Y.; Flavin, M. T.; Xu, Z. Q. J. Org. Chem. 1996, 61, 7697. Peterson olefination: (j) Washbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1996, 52, 14199.
24. Hydrophosphorylation of terminal alkynes: (a) Zhao, C.-Q.; Han, L. B.; Goto, M.; Tanaka, M. Angew Chem., Int. Ed. 2001, 40, 1929. (b) Han, L. B. Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. Zirconation of alkynylphosphonates: (c) Quntar, A. A. A.; Melman, A.; Srebnik, M. J. Org. Chem. 2002, 67, 3769. Carbocupration: (d) Gil, J. M.; Oh, D. Y. J. Org. Chem. 1999, 64, 2950. Catalytic hydrogenation of alkynylphosphonates (e) Cristau, H.-J.; Mbianda, X. Y.; Beziat, Y.; Gasc, M. B. J. Organomet. Chem. 1997, 529, 301. Radical trapping: (f) Jiao, X.-Y.; Bentrude, W. G. J. Am. Chem. Soc. 1999, 121, 6088. Allylic rearrangement: (g) Muthiah, C.; Kumar, K. P.; Mani, C. A.; Swamy, K. C. K. J. Org. Chem. 2000, 65, 3733. Triflation: (h) Okauchi, T.; Yano, T.; Fukamachi, T.; Ichikawa, J.; Minami, T. Tetrahedron Lett. 1999, 40, 5337. Wittig: (i) Xu, Y.; Flavin, M. T.; Xu, Z. Q. J. Org. Chem. 1996, 61, 7697. Peterson olefination: (j) Washbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1996, 52, 14199.
25. Hydrophosphorylation of terminal alkynes: (a) Zhao, C.-Q.; Han, L. B.; Goto, M.; Tanaka, M. Angew Chem., Int. Ed. 2001, 40, 1929. (b) Han, L. B. Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. Zirconation of alkynylphosphonates: (c) Quntar, A. A. A.; Melman, A.; Srebnik, M. J. Org. Chem. 2002, 67, 3769. Carbocupration: (d) Gil, J. M.; Oh, D. Y. J. Org. Chem. 1999, 64, 2950. Catalytic hydrogenation of alkynylphosphonates (e) Cristau, H.-J.; Mbianda, X. Y.; Beziat, Y.; Gasc, M. B. J. Organomet. Chem. 1997, 529, 301. Radical trapping: (f) Jiao, X.-Y.; Bentrude, W. G. J. Am. Chem. Soc. 1999, 121, 6088. Allylic rearrangement: (g) Muthiah, C.; Kumar, K. P.; Mani, C. A.; Swamy, K. C. K. J. Org. Chem. 2000, 65, 3733. Triflation: (h) Okauchi, T.; Yano, T.; Fukamachi, T.; Ichikawa, J.; Minami, T. Tetrahedron Lett. 1999, 40, 5337. Wittig: (i) Xu, Y.; Flavin, M. T.; Xu, Z. Q. J. Org. Chem. 1996, 61, 7697. Peterson olefination: (j) Washbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1996, 52, 14199.
26. Hydrophosphorylation of terminal alkynes: (a) Zhao, C.-Q.; Han, L. B.; Goto, M.; Tanaka, M. Angew Chem., Int. Ed. 2001, 40, 1929. (b) Han, L. B. Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. Zirconation of alkynylphosphonates: (c) Quntar, A. A. A.; Melman, A.; Srebnik, M. J. Org. Chem. 2002, 67, 3769. Carbocupration: (d) Gil, J. M.; Oh, D. Y. J. Org. Chem. 1999, 64, 2950. Catalytic hydrogenation of alkynylphosphonates (e) Cristau, H.-J.; Mbianda, X. Y.; Beziat, Y.; Gasc, M. B. J. Organomet. Chem. 1997, 529, 301. Radical trapping: (f) Jiao, X.-Y.; Bentrude, W. G. J. Am. Chem. Soc. 1999, 121, 6088. Allylic rearrangement: (g) Muthiah, C.; Kumar, K. P.; Mani, C. A.; Swamy, K. C. K. J. Org. Chem. 2000, 65, 3733. Triflation: (h) Okauchi, T.; Yano, T.; Fukamachi, T.; Ichikawa, J.; Minami, T. Tetrahedron Lett. 1999, 40, 5337. Wittig: (i) Xu, Y.; Flavin, M. T.; Xu, Z. Q. J. Org. Chem. 1996, 61, 7697. Peterson olefination: (j) Washbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1996, 52, 14199.
27. Hydrophosphorylation of terminal alkynes: (a) Zhao, C.-Q.; Han, L. B.; Goto, M.; Tanaka, M. Angew Chem., Int. Ed. 2001, 40, 1929. (b) Han, L. B. Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. Zirconation of alkynylphosphonates: (c) Quntar, A. A. A.; Melman, A.; Srebnik, M. J. Org. Chem. 2002, 67, 3769. Carbocupration: (d) Gil, J. M.; Oh, D. Y. J. Org. Chem. 1999, 64, 2950. Catalytic hydrogenation of alkynylphosphonates (e) Cristau, H.-J.; Mbianda, X. Y.; Beziat, Y.; Gasc, M. B. J. Organomet. Chem. 1997, 529, 301. Radical trapping: (f) Jiao, X.-Y.; Bentrude, W. G. J. Am. Chem. Soc. 1999, 121, 6088. Allylic rearrangement: (g) Muthiah, C.; Kumar, K. P.; Mani, C. A.; Swamy, K. C. K. J. Org. Chem. 2000, 65, 3733. Triflation: (h) Okauchi, T.; Yano, T.; Fukamachi, T.; Ichikawa, J.; Minami, T. Tetrahedron Lett. 1999, 40, 5337. Wittig: (i) Xu, Y.; Flavin, M. T.; Xu, Z. Q. J. Org. Chem. 1996, 61, 7697. Peterson olefination: (j) Washbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1996, 52, 14199.
28. Hydrophosphorylation of terminal alkynes: (a) Zhao, C.-Q.; Han, L. B.; Goto, M.; Tanaka, M. Angew Chem., Int. Ed. 2001, 40, 1929. (b) Han, L. B. Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. Zirconation of alkynylphosphonates: (c) Quntar, A. A. A.; Melman, A.; Srebnik, M. J. Org. Chem. 2002, 67, 3769. Carbocupration: (d) Gil, J. M.; Oh, D. Y. J. Org. Chem. 1999, 64, 2950. Catalytic hydrogenation of alkynylphosphonates (e) Cristau, H.-J.; Mbianda, X. Y.; Beziat, Y.; Gasc, M. B. J. Organomet. Chem. 1997, 529, 301. Radical trapping: (f) Jiao, X.-Y.; Bentrude, W. G. J. Am. Chem. Soc. 1999, 121, 6088. Allylic rearrangement: (g) Muthiah, C.; Kumar, K. P.; Mani, C. A.; Swamy, K. C. K. J. Org. Chem. 2000, 65, 3733. Triflation: (h) Okauchi, T.; Yano, T.; Fukamachi, T.; Ichikawa, J.; Minami, T. Tetrahedron Lett. 1999, 40, 5337. Wittig: (i) Xu, Y.; Flavin, M. T.; Xu, Z. Q. J. Org. Chem. 1996, 61, 7697. Peterson olefination: (j) Washbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1996, 52, 14199.
29. Hydrophosphorylation of terminal alkynes: (a) Zhao, C.-Q.; Han, L. B.; Goto, M.; Tanaka, M. Angew Chem., Int. Ed. 2001, 40, 1929. (b) Han, L. B. Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. Zirconation of alkynylphosphonates: (c) Quntar, A. A. A.; Melman, A.; Srebnik, M. J. Org. Chem. 2002, 67, 3769. Carbocupration: (d) Gil, J. M.; Oh, D. Y. J. Org. Chem. 1999, 64, 2950. Catalytic hydrogenation of alkynylphosphonates (e) Cristau, H.-J.; Mbianda, X. Y.; Beziat, Y.; Gasc, M. B. J. Organomet. Chem. 1997, 529, 301. Radical trapping: (f) Jiao, X.-Y.; Bentrude, W. G. J. Am. Chem. Soc. 1999, 121, 6088. Allylic rearrangement: (g) Muthiah, C.; Kumar, K. P.; Mani, C. A.; Swamy, K. C. K. J. Org. Chem. 2000, 65, 3733. Triflation: (h) Okauchi, T.; Yano, T.; Fukamachi, T.; Ichikawa, J.; Minami, T. Tetrahedron Lett. 1999, 40, 5337. Wittig: (i) Xu, Y.; Flavin, M. T.; Xu, Z. Q. J. Org. Chem. 1996, 61, 7697. Peterson olefination: (j) Washbusch, R.; Carran, J.; Savignac, P. Tetrahedron 1996, 52, 14199.
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