Remarkable Stereocontrol in the Palladium-Catalysed Cyclopropanation of Vinyl- and Dienylboronates by Substituted Diazoalkanes

Advanced Synthesis and Catalysis

Volumn 344, Issue 10, 2002, Pages 1063-1067

  Markó, István E ^a   Kumamoto, Takuya ^a   Giard, Thierry ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

Ambruticin; Boronates; Cyclopropanation; Diastereoselectivity; Diazoalkanes; Palladium

Indexed keywords

EID: 0042452187     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200212)344:10<1063::AID-ADSC1063>3.0.CO;2-L     Document Type: Article

References (40)

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22. 2, see: a) C. Rodriguez-Garcia, J. Ibarzo, A. Alvarez-Larena, V. Branchadell, A. Oliva, R. M. Ortuno, Tetrahedron 2001, 57, 1025; b) U. M. Dzhemilev, V. A. Dokichev, S. Z. Sultanov, S. L. Khursan, O. M. Nefedov, Y. V. Tomilov, A. B. Kostitsyn, Izv. Akad. Nauk. Ser. Khim. 1992, 2353; c) O. M. Nefedov, Y. V. Tomilov, A. B. Kostitsyn, U. M. Dzhemilev, V. A. Dokichev, Mendeleev Commun. 1992, 13; d) U. Mende, B. Radüchel, W. Skuballa, H. Vorbrüggen, Tetrahedron Lett. 1975, 16, 629; e) R. M. Ortuno, J. Ibarzo, A. Alvarez-Larena, J. F. Piniella, Tetrahedron Lett. 1996, 37, 4059; f) H. Abdallah, R. Grée, R. Carrié, Tetrahedron Lett. 1982, 23, 503; g) P. Fontani, B. Carboni, M. Vaultier, R. Carrié, Tetrahedron Lett. 1989, 30, 4815; h) P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605; i) J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893.
23. 2, see: a) C. Rodriguez-Garcia, J. Ibarzo, A. Alvarez-Larena, V. Branchadell, A. Oliva, R. M. Ortuno, Tetrahedron 2001, 57, 1025; b) U. M. Dzhemilev, V. A. Dokichev, S. Z. Sultanov, S. L. Khursan, O. M. Nefedov, Y. V. Tomilov, A. B. Kostitsyn, Izv. Akad. Nauk. Ser. Khim. 1992, 2353; c) O. M. Nefedov, Y. V. Tomilov, A. B. Kostitsyn, U. M. Dzhemilev, V. A. Dokichev, Mendeleev Commun. 1992, 13; d) U. Mende, B. Radüchel, W. Skuballa, H. Vorbrüggen, Tetrahedron Lett. 1975, 16, 629; e) R. M. Ortuno, J. Ibarzo, A. Alvarez-Larena, J. F. Piniella, Tetrahedron Lett. 1996, 37, 4059; f) H. Abdallah, R. Grée, R. Carrié, Tetrahedron Lett. 1982, 23, 503; g) P. Fontani, B. Carboni, M. Vaultier, R. Carrié, Tetrahedron Lett. 1989, 30, 4815; h) P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605; i) J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893.
24. 2, see: a) C. Rodriguez-Garcia, J. Ibarzo, A. Alvarez-Larena, V. Branchadell, A. Oliva, R. M. Ortuno, Tetrahedron 2001, 57, 1025; b) U. M. Dzhemilev, V. A. Dokichev, S. Z. Sultanov, S. L. Khursan, O. M. Nefedov, Y. V. Tomilov, A. B. Kostitsyn, Izv. Akad. Nauk. Ser. Khim. 1992, 2353; c) O. M. Nefedov, Y. V. Tomilov, A. B. Kostitsyn, U. M. Dzhemilev, V. A. Dokichev, Mendeleev Commun. 1992, 13; d) U. Mende, B. Radüchel, W. Skuballa, H. Vorbrüggen, Tetrahedron Lett. 1975, 16, 629; e) R. M. Ortuno, J. Ibarzo, A. Alvarez-Larena, J. F. Piniella, Tetrahedron Lett. 1996, 37, 4059; f) H. Abdallah, R. Grée, R. Carrié, Tetrahedron Lett. 1982, 23, 503; g) P. Fontani, B. Carboni, M. Vaultier, R. Carrié, Tetrahedron Lett. 1989, 30, 4815; h) P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605; i) J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893.
25. 2, see: a) C. Rodriguez-Garcia, J. Ibarzo, A. Alvarez-Larena, V. Branchadell, A. Oliva, R. M. Ortuno, Tetrahedron 2001, 57, 1025; b) U. M. Dzhemilev, V. A. Dokichev, S. Z. Sultanov, S. L. Khursan, O. M. Nefedov, Y. V. Tomilov, A. B. Kostitsyn, Izv. Akad. Nauk. Ser. Khim. 1992, 2353; c) O. M. Nefedov, Y. V. Tomilov, A. B. Kostitsyn, U. M. Dzhemilev, V. A. Dokichev, Mendeleev Commun. 1992, 13; d) U. Mende, B. Radüchel, W. Skuballa, H. Vorbrüggen, Tetrahedron Lett. 1975, 16, 629; e) R. M. Ortuno, J. Ibarzo, A. Alvarez-Larena, J. F. Piniella, Tetrahedron Lett. 1996, 37, 4059; f) H. Abdallah, R. Grée, R. Carrié, Tetrahedron Lett. 1982, 23, 503; g) P. Fontani, B. Carboni, M. Vaultier, R. Carrié, Tetrahedron Lett. 1989, 30, 4815; h) P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605; i) J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893.
26. 2, see: a) C. Rodriguez-Garcia, J. Ibarzo, A. Alvarez-Larena, V. Branchadell, A. Oliva, R. M. Ortuno, Tetrahedron 2001, 57, 1025; b) U. M. Dzhemilev, V. A. Dokichev, S. Z. Sultanov, S. L. Khursan, O. M. Nefedov, Y. V. Tomilov, A. B. Kostitsyn, Izv. Akad. Nauk. Ser. Khim. 1992, 2353; c) O. M. Nefedov, Y. V. Tomilov, A. B. Kostitsyn, U. M. Dzhemilev, V. A. Dokichev, Mendeleev Commun. 1992, 13; d) U. Mende, B. Radüchel, W. Skuballa, H. Vorbrüggen, Tetrahedron Lett. 1975, 16, 629; e) R. M. Ortuno, J. Ibarzo, A. Alvarez-Larena, J. F. Piniella, Tetrahedron Lett. 1996, 37, 4059; f) H. Abdallah, R. Grée, R. Carrié, Tetrahedron Lett. 1982, 23, 503; g) P. Fontani, B. Carboni, M. Vaultier, R. Carrié, Tetrahedron Lett. 1989, 30, 4815; h) P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605; i) J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893.
27. 2, see: a) C. Rodriguez-Garcia, J. Ibarzo, A. Alvarez-Larena, V. Branchadell, A. Oliva, R. M. Ortuno, Tetrahedron 2001, 57, 1025; b) U. M. Dzhemilev, V. A. Dokichev, S. Z. Sultanov, S. L. Khursan, O. M. Nefedov, Y. V. Tomilov, A. B. Kostitsyn, Izv. Akad. Nauk. Ser. Khim. 1992, 2353; c) O. M. Nefedov, Y. V. Tomilov, A. B. Kostitsyn, U. M. Dzhemilev, V. A. Dokichev, Mendeleev Commun. 1992, 13; d) U. Mende, B. Radüchel, W. Skuballa, H. Vorbrüggen, Tetrahedron Lett. 1975, 16, 629; e) R. M. Ortuno, J. Ibarzo, A. Alvarez-Larena, J. F. Piniella, Tetrahedron Lett. 1996, 37, 4059; f) H. Abdallah, R. Grée, R. Carrié, Tetrahedron Lett. 1982, 23, 503; g) P. Fontani, B. Carboni, M. Vaultier, R. Carrié, Tetrahedron Lett. 1989, 30, 4815; h) P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605; i) J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893.
28. 2, see: a) C. Rodriguez-Garcia, J. Ibarzo, A. Alvarez-Larena, V. Branchadell, A. Oliva, R. M. Ortuno, Tetrahedron 2001, 57, 1025; b) U. M. Dzhemilev, V. A. Dokichev, S. Z. Sultanov, S. L. Khursan, O. M. Nefedov, Y. V. Tomilov, A. B. Kostitsyn, Izv. Akad. Nauk. Ser. Khim. 1992, 2353; c) O. M. Nefedov, Y. V. Tomilov, A. B. Kostitsyn, U. M. Dzhemilev, V. A. Dokichev, Mendeleev Commun. 1992, 13; d) U. Mende, B. Radüchel, W. Skuballa, H. Vorbrüggen, Tetrahedron Lett. 1975, 16, 629; e) R. M. Ortuno, J. Ibarzo, A. Alvarez-Larena, J. F. Piniella, Tetrahedron Lett. 1996, 37, 4059; f) H. Abdallah, R. Grée, R. Carrié, Tetrahedron Lett. 1982, 23, 503; g) P. Fontani, B. Carboni, M. Vaultier, R. Carrié, Tetrahedron Lett. 1989, 30, 4815; h) P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605; i) J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893.
29. 2, see: a) C. Rodriguez-Garcia, J. Ibarzo, A. Alvarez-Larena, V. Branchadell, A. Oliva, R. M. Ortuno, Tetrahedron 2001, 57, 1025; b) U. M. Dzhemilev, V. A. Dokichev, S. Z. Sultanov, S. L. Khursan, O. M. Nefedov, Y. V. Tomilov, A. B. Kostitsyn, Izv. Akad. Nauk. Ser. Khim. 1992, 2353; c) O. M. Nefedov, Y. V. Tomilov, A. B. Kostitsyn, U. M. Dzhemilev, V. A. Dokichev, Mendeleev Commun. 1992, 13; d) U. Mende, B. Radüchel, W. Skuballa, H. Vorbrüggen, Tetrahedron Lett. 1975, 16, 629; e) R. M. Ortuno, J. Ibarzo, A. Alvarez-Larena, J. F. Piniella, Tetrahedron Lett. 1996, 37, 4059; f) H. Abdallah, R. Grée, R. Carrié, Tetrahedron Lett. 1982, 23, 503; g) P. Fontani, B. Carboni, M. Vaultier, R. Carrié, Tetrahedron Lett. 1989, 30, 4815; h) P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605; i) J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893.
30. For selected references on the asymmetric cyclopropanation of vinylboronates, see: a) T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986; b) J. E. A. Luithle, J. Pietruszka, Liebigs Ann./Recueil 1997, 2297; c) A. B. Charrette, R. P. De Freitas-Gil, Tetrahedron Lett. 1997, 38, 2809; d) S.-M. Zhou, M.-Z; Deng, L.-J. Xia, M.-H. Tang, Angew. Chem. Int. Ed. 1998, 37, 2845; e) J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 1999, 64, 8287; f) J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 2000, 65, 9194; g) J. Pietruszka, A. Witt, J. Chem. Soc. Perkin Trans. 1 2000, 4293.
31. For selected references on the asymmetric cyclopropanation of vinylboronates, see: a) T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986; b) J. E. A. Luithle, J. Pietruszka, Liebigs Ann./Recueil 1997, 2297; c) A. B. Charrette, R. P. De Freitas-Gil, Tetrahedron Lett. 1997, 38, 2809; d) S.-M. Zhou, M.-Z; Deng, L.-J. Xia, M.-H. Tang, Angew. Chem. Int. Ed. 1998, 37, 2845; e) J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 1999, 64, 8287; f) J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 2000, 65, 9194; g) J. Pietruszka, A. Witt, J. Chem. Soc. Perkin Trans. 1 2000, 4293.
32. For selected references on the asymmetric cyclopropanation of vinylboronates, see: a) T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986; b) J. E. A. Luithle, J. Pietruszka, Liebigs Ann./Recueil 1997, 2297; c) A. B. Charrette, R. P. De Freitas-Gil, Tetrahedron Lett. 1997, 38, 2809; d) S.-M. Zhou, M.-Z; Deng, L.-J. Xia, M.-H. Tang, Angew. Chem. Int. Ed. 1998, 37, 2845; e) J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 1999, 64, 8287; f) J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 2000, 65, 9194; g) J. Pietruszka, A. Witt, J. Chem. Soc. Perkin Trans. 1 2000, 4293.
33. For selected references on the asymmetric cyclopropanation of vinylboronates, see: a) T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986; b) J. E. A. Luithle, J. Pietruszka, Liebigs Ann./Recueil 1997, 2297; c) A. B. Charrette, R. P. De Freitas-Gil, Tetrahedron Lett. 1997, 38, 2809; d) S.-M. Zhou, M.-Z; Deng, L.-J. Xia, M.-H. Tang, Angew. Chem. Int. Ed. 1998, 37, 2845; e) J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 1999, 64, 8287; f) J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 2000, 65, 9194; g) J. Pietruszka, A. Witt, J. Chem. Soc. Perkin Trans. 1 2000, 4293.
34. For selected references on the asymmetric cyclopropanation of vinylboronates, see: a) T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986; b) J. E. A. Luithle, J. Pietruszka, Liebigs Ann./Recueil 1997, 2297; c) A. B. Charrette, R. P. De Freitas-Gil, Tetrahedron Lett. 1997, 38, 2809; d) S.-M. Zhou, M.-Z; Deng, L.-J. Xia, M.-H. Tang, Angew. Chem. Int. Ed. 1998, 37, 2845; e) J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 1999, 64, 8287; f) J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 2000, 65, 9194; g) J. Pietruszka, A. Witt, J. Chem. Soc. Perkin Trans. 1 2000, 4293.
35. For selected references on the asymmetric cyclopropanation of vinylboronates, see: a) T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986; b) J. E. A. Luithle, J. Pietruszka, Liebigs Ann./Recueil 1997, 2297; c) A. B. Charrette, R. P. De Freitas-Gil, Tetrahedron Lett. 1997, 38, 2809; d) S.-M. Zhou, M.-Z; Deng, L.-J. Xia, M.-H. Tang, Angew. Chem. Int. Ed. 1998, 37, 2845; e) J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 1999, 64, 8287; f) J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 2000, 65, 9194; g) J. Pietruszka, A. Witt, J. Chem. Soc. Perkin Trans. 1 2000, 4293.
36. For selected references on the asymmetric cyclopropanation of vinylboronates, see: a) T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986; b) J. E. A. Luithle, J. Pietruszka, Liebigs Ann./Recueil 1997, 2297; c) A. B. Charrette, R. P. De Freitas-Gil, Tetrahedron Lett. 1997, 38, 2809; d) S.-M. Zhou, M.-Z; Deng, L.-J. Xia, M.-H. Tang, Angew. Chem. Int. Ed. 1998, 37, 2845; e) J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 1999, 64, 8287; f) J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 2000, 65, 9194; g) J. Pietruszka, A. Witt, J. Chem. Soc. Perkin Trans. 1 2000, 4293.
37. For some interesting discussions on the mechanism of these palladium-catalysed cyclopropanation reactions, see: a) S. E. Denmark, R. A. Stavenger, A. M. Faucher, P. E. Edwards, J. Org. Chem. 1997, 62, 3375; b) C. Rodriguez-Garcia, A. Oliva, R. M. Ortuno, V. Branchadell, J. Am. Chem. Soc. 2001, 123, 6157.
38. For some interesting discussions on the mechanism of these palladium-catalysed cyclopropanation reactions, see: a) S. E. Denmark, R. A. Stavenger, A. M. Faucher, P. E. Edwards, J. Org. Chem. 1997, 62, 3375; b) C. Rodriguez-Garcia, A. Oliva, R. M. Ortuno, V. Branchadell, J. Am. Chem. Soc. 2001, 123, 6157.
39. K. Nakayama, J. D. Rainier, Tetrahedron 1990, 46, 4165.
40. [11e]). Chemical correlation to establish unambiguously the absolute stereochemistry of 10 is currently underway.