Regio- and stereocontrolled formation of chiral epoxy oxazolidines via bromocarbamation of N-Boc alkenyl oxazolidines. Application to asymmetric synthesis

Journal of Organic Chemistry

Volumn 62, Issue 7, 1997, Pages 2106-2112

  Agami, Claude ^a   Couty, François ^a   Hamon, Louis ^a   Venier, Olivier ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; OXAZOLIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030996162     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962277g     Document Type: Article

References (60)

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2. For some recent examples, see: (a) Meyers, A. I.; Seefeld, M. A.; Lefker, B. A. J. Org. Chem. 1996, 61, 5712-5713. (b) Andrews, M. D.; Brewster, A. G.; Moloney, M. G. Synlett 1996, 612-614. (c) Roth, G. P.; Leonard, S. F.; Tong, L. J. Org. Chem. 1996, 61, 5710-5711. (d) Amat, M.; Llor, N.; Hidalgo, J.; Bosch, J.; Molins, E.; Miravittles, C. Tetrahedron: Asymmetry 1996, 7, 2501-2504. (e) Froelich, O.; Desos, P.; Bonin, M.; Quirion, J. C.; Husson, H. P.; Zhu, J. J. Org. Chem. 1996, 61, 6700-6705. (f) Garcia-Valverde, M.; Pedrosa, R.; Vicente, M.; Garcia-Granda, S.; Guttierez-Rodriguez, A. Tetrahedron 1996, 52, 10761-10770. (g) O'Brien, P.; Warren, S. Tetrahedron Lett. 1996, 37, 3051-3054. (h) Agami, C.; Mathieu, H.; Couty, F. Tetrahedron Lett. 1996, 37, 4001-4002.
3. For some recent examples, see: (a) Meyers, A. I.; Seefeld, M. A.; Lefker, B. A. J. Org. Chem. 1996, 61, 5712-5713. (b) Andrews, M. D.; Brewster, A. G.; Moloney, M. G. Synlett 1996, 612-614. (c) Roth, G. P.; Leonard, S. F.; Tong, L. J. Org. Chem. 1996, 61, 5710-5711. (d) Amat, M.; Llor, N.; Hidalgo, J.; Bosch, J.; Molins, E.; Miravittles, C. Tetrahedron: Asymmetry 1996, 7, 2501-2504. (e) Froelich, O.; Desos, P.; Bonin, M.; Quirion, J. C.; Husson, H. P.; Zhu, J. J. Org. Chem. 1996, 61, 6700-6705. (f) Garcia-Valverde, M.; Pedrosa, R.; Vicente, M.; Garcia-Granda, S.; Guttierez-Rodriguez, A. Tetrahedron 1996, 52, 10761-10770. (g) O'Brien, P.; Warren, S. Tetrahedron Lett. 1996, 37, 3051-3054. (h) Agami, C.; Mathieu, H.; Couty, F. Tetrahedron Lett. 1996, 37, 4001-4002.
4. For some recent examples, see: (a) Meyers, A. I.; Seefeld, M. A.; Lefker, B. A. J. Org. Chem. 1996, 61, 5712-5713. (b) Andrews, M. D.; Brewster, A. G.; Moloney, M. G. Synlett 1996, 612-614. (c) Roth, G. P.; Leonard, S. F.; Tong, L. J. Org. Chem. 1996, 61, 5710-5711. (d) Amat, M.; Llor, N.; Hidalgo, J.; Bosch, J.; Molins, E.; Miravittles, C. Tetrahedron: Asymmetry 1996, 7, 2501-2504. (e) Froelich, O.; Desos, P.; Bonin, M.; Quirion, J. C.; Husson, H. P.; Zhu, J. J. Org. Chem. 1996, 61, 6700-6705. (f) Garcia-Valverde, M.; Pedrosa, R.; Vicente, M.; Garcia-Granda, S.; Guttierez-Rodriguez, A. Tetrahedron 1996, 52, 10761-10770. (g) O'Brien, P.; Warren, S. Tetrahedron Lett. 1996, 37, 3051-3054. (h) Agami, C.; Mathieu, H.; Couty, F. Tetrahedron Lett. 1996, 37, 4001-4002.
5. For some recent examples, see: (a) Meyers, A. I.; Seefeld, M. A.; Lefker, B. A. J. Org. Chem. 1996, 61, 5712-5713. (b) Andrews, M. D.; Brewster, A. G.; Moloney, M. G. Synlett 1996, 612-614. (c) Roth, G. P.; Leonard, S. F.; Tong, L. J. Org. Chem. 1996, 61, 5710-5711. (d) Amat, M.; Llor, N.; Hidalgo, J.; Bosch, J.; Molins, E.; Miravittles, C. Tetrahedron: Asymmetry 1996, 7, 2501-2504. (e) Froelich, O.; Desos, P.; Bonin, M.; Quirion, J. C.; Husson, H. P.; Zhu, J. J. Org. Chem. 1996, 61, 6700-6705. (f) Garcia-Valverde, M.; Pedrosa, R.; Vicente, M.; Garcia-Granda, S.; Guttierez-Rodriguez, A. Tetrahedron 1996, 52, 10761-10770. (g) O'Brien, P.; Warren, S. Tetrahedron Lett. 1996, 37, 3051-3054. (h) Agami, C.; Mathieu, H.; Couty, F. Tetrahedron Lett. 1996, 37, 4001-4002.
6. For some recent examples, see: (a) Meyers, A. I.; Seefeld, M. A.; Lefker, B. A. J. Org. Chem. 1996, 61, 5712-5713. (b) Andrews, M. D.; Brewster, A. G.; Moloney, M. G. Synlett 1996, 612-614. (c) Roth, G. P.; Leonard, S. F.; Tong, L. J. Org. Chem. 1996, 61, 5710-5711. (d) Amat, M.; Llor, N.; Hidalgo, J.; Bosch, J.; Molins, E.; Miravittles, C. Tetrahedron: Asymmetry 1996, 7, 2501-2504. (e) Froelich, O.; Desos, P.; Bonin, M.; Quirion, J. C.; Husson, H. P.; Zhu, J. J. Org. Chem. 1996, 61, 6700-6705. (f) Garcia-Valverde, M.; Pedrosa, R.; Vicente, M.; Garcia-Granda, S.; Guttierez-Rodriguez, A. Tetrahedron 1996, 52, 10761-10770. (g) O'Brien, P.; Warren, S. Tetrahedron Lett. 1996, 37, 3051-3054. (h) Agami, C.; Mathieu, H.; Couty, F. Tetrahedron Lett. 1996, 37, 4001-4002.
7. For some recent examples, see: (a) Meyers, A. I.; Seefeld, M. A.; Lefker, B. A. J. Org. Chem. 1996, 61, 5712-5713. (b) Andrews, M. D.; Brewster, A. G.; Moloney, M. G. Synlett 1996, 612-614. (c) Roth, G. P.; Leonard, S. F.; Tong, L. J. Org. Chem. 1996, 61, 5710-5711. (d) Amat, M.; Llor, N.; Hidalgo, J.; Bosch, J.; Molins, E.; Miravittles, C. Tetrahedron: Asymmetry 1996, 7, 2501-2504. (e) Froelich, O.; Desos, P.; Bonin, M.; Quirion, J. C.; Husson, H. P.; Zhu, J. J. Org. Chem. 1996, 61, 6700-6705. (f) Garcia-Valverde, M.; Pedrosa, R.; Vicente, M.; Garcia-Granda, S.; Guttierez-Rodriguez, A. Tetrahedron 1996, 52, 10761-10770. (g) O'Brien, P.; Warren, S. Tetrahedron Lett. 1996, 37, 3051-3054. (h) Agami, C.; Mathieu, H.; Couty, F. Tetrahedron Lett. 1996, 37, 4001-4002.
8. For some recent examples, see: (a) Meyers, A. I.; Seefeld, M. A.; Lefker, B. A. J. Org. Chem. 1996, 61, 5712-5713. (b) Andrews, M. D.; Brewster, A. G.; Moloney, M. G. Synlett 1996, 612-614. (c) Roth, G. P.; Leonard, S. F.; Tong, L. J. Org. Chem. 1996, 61, 5710-5711. (d) Amat, M.; Llor, N.; Hidalgo, J.; Bosch, J.; Molins, E.; Miravittles, C. Tetrahedron: Asymmetry 1996, 7, 2501-2504. (e) Froelich, O.; Desos, P.; Bonin, M.; Quirion, J. C.; Husson, H. P.; Zhu, J. J. Org. Chem. 1996, 61, 6700-6705. (f) Garcia-Valverde, M.; Pedrosa, R.; Vicente, M.; Garcia-Granda, S.; Guttierez-Rodriguez, A. Tetrahedron 1996, 52, 10761-10770. (g) O'Brien, P.; Warren, S. Tetrahedron Lett. 1996, 37, 3051-3054. (h) Agami, C.; Mathieu, H.; Couty, F. Tetrahedron Lett. 1996, 37, 4001-4002.
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12. Preliminary communication: Agami, C.; Couty, F.; Venier, O. Synlett 1995, 1027-1028.
13. For other examples related to nucleophilic reactivity of carbamate moieties, see: (a) Agami, C.; Couty, F.; Hamon, L.; Venier, O. Tetrahedron Lett. 1993, 34, 4509-4512. (b) Curran, T. P.; Pollastri, M. P.; Abelleira, S. M.; Messier, R. J.; McCollum, T. A. Tetrahedron Lett. 1994, 35, 5409-5412. (c) Campanini, L.; Duréault, A.; Depezay, J. C. Tetrahedron Lett. 1995, 36, 8015-8018. (d) Vanucci, C.; Brusson, X.; Verdel, V.; Zana, F.; Dhimane, H.; Lhommet, G. Tetrahedron Lett. 1995, 36, 2971-2974. (d) Haddad, M.; Larcheveque, M. Tetrahedron Lett. 1996, 37, 4525-4528. (e) Lee, J. W.; Lee, J. H.; Son, H. J.; Choi, Y. K.; Yoon, G. J.; Park, M. H. Synth. Commun. 1996, 26, 83-88. (f) Sepulveda-Arques, J.; Armero-Alarte, T.; Acero-Alarcon, A.; Zaballos-Garcia, E.; Solesio, B. Y.; Carrera, J. E. Tetrahedron 1996, 52, 2097-2102. (g) Williams, L.; Zhang, Z.; Shao, F.; Caroll, F. J.; Joullié, M. M. Tetrahedron 1996, 52, 11673-11694.
14. For other examples related to nucleophilic reactivity of carbamate moieties, see: (a) Agami, C.; Couty, F.; Hamon, L.; Venier, O. Tetrahedron Lett. 1993, 34, 4509-4512. (b) Curran, T. P.; Pollastri, M. P.; Abelleira, S. M.; Messier, R. J.; McCollum, T. A. Tetrahedron Lett. 1994, 35, 5409-5412. (c) Campanini, L.; Duréault, A.; Depezay, J. C. Tetrahedron Lett. 1995, 36, 8015-8018. (d) Vanucci, C.; Brusson, X.; Verdel, V.; Zana, F.; Dhimane, H.; Lhommet, G. Tetrahedron Lett. 1995, 36, 2971-2974. (d) Haddad, M.; Larcheveque, M. Tetrahedron Lett. 1996, 37, 4525-4528. (e) Lee, J. W.; Lee, J. H.; Son, H. J.; Choi, Y. K.; Yoon, G. J.; Park, M. H. Synth. Commun. 1996, 26, 83-88. (f) Sepulveda-Arques, J.; Armero-Alarte, T.; Acero-Alarcon, A.; Zaballos-Garcia, E.; Solesio, B. Y.; Carrera, J. E. Tetrahedron 1996, 52, 2097-2102. (g) Williams, L.; Zhang, Z.; Shao, F.; Caroll, F. J.; Joullié, M. M. Tetrahedron 1996, 52, 11673-11694.
15. For other examples related to nucleophilic reactivity of carbamate moieties, see: (a) Agami, C.; Couty, F.; Hamon, L.; Venier, O. Tetrahedron Lett. 1993, 34, 4509-4512. (b) Curran, T. P.; Pollastri, M. P.; Abelleira, S. M.; Messier, R. J.; McCollum, T. A. Tetrahedron Lett. 1994, 35, 5409-5412. (c) Campanini, L.; Duréault, A.; Depezay, J. C. Tetrahedron Lett. 1995, 36, 8015-8018. (d) Vanucci, C.; Brusson, X.; Verdel, V.; Zana, F.; Dhimane, H.; Lhommet, G. Tetrahedron Lett. 1995, 36, 2971-2974. (d) Haddad, M.; Larcheveque, M. Tetrahedron Lett. 1996, 37, 4525-4528. (e) Lee, J. W.; Lee, J. H.; Son, H. J.; Choi, Y. K.; Yoon, G. J.; Park, M. H. Synth. Commun. 1996, 26, 83-88. (f) Sepulveda-Arques, J.; Armero-Alarte, T.; Acero-Alarcon, A.; Zaballos-Garcia, E.; Solesio, B. Y.; Carrera, J. E. Tetrahedron 1996, 52, 2097-2102. (g) Williams, L.; Zhang, Z.; Shao, F.; Caroll, F. J.; Joullié, M. M. Tetrahedron 1996, 52, 11673-11694.
16. For other examples related to nucleophilic reactivity of carbamate moieties, see: (a) Agami, C.; Couty, F.; Hamon, L.; Venier, O. Tetrahedron Lett. 1993, 34, 4509-4512. (b) Curran, T. P.; Pollastri, M. P.; Abelleira, S. M.; Messier, R. J.; McCollum, T. A. Tetrahedron Lett. 1994, 35, 5409-5412. (c) Campanini, L.; Duréault, A.; Depezay, J. C. Tetrahedron Lett. 1995, 36, 8015-8018. (d) Vanucci, C.; Brusson, X.; Verdel, V.; Zana, F.; Dhimane, H.; Lhommet, G. Tetrahedron Lett. 1995, 36, 2971-2974. (d) Haddad, M.; Larcheveque, M. Tetrahedron Lett. 1996, 37, 4525-4528. (e) Lee, J. W.; Lee, J. H.; Son, H. J.; Choi, Y. K.; Yoon, G. J.; Park, M. H. Synth. Commun. 1996, 26, 83-88. (f) Sepulveda-Arques, J.; Armero-Alarte, T.; Acero-Alarcon, A.; Zaballos-Garcia, E.; Solesio, B. Y.; Carrera, J. E. Tetrahedron 1996, 52, 2097-2102. (g) Williams, L.; Zhang, Z.; Shao, F.; Caroll, F. J.; Joullié, M. M. Tetrahedron 1996, 52, 11673-11694.
17. For other examples related to nucleophilic reactivity of carbamate moieties, see: (a) Agami, C.; Couty, F.; Hamon, L.; Venier, O. Tetrahedron Lett. 1993, 34, 4509-4512. (b) Curran, T. P.; Pollastri, M. P.; Abelleira, S. M.; Messier, R. J.; McCollum, T. A. Tetrahedron Lett. 1994, 35, 5409-5412. (c) Campanini, L.; Duréault, A.; Depezay, J. C. Tetrahedron Lett. 1995, 36, 8015-8018. (d) Vanucci, C.; Brusson, X.; Verdel, V.; Zana, F.; Dhimane, H.; Lhommet, G. Tetrahedron Lett. 1995, 36, 2971-2974. (d) Haddad, M.; Larcheveque, M. Tetrahedron Lett. 1996, 37, 4525-4528. (e) Lee, J. W.; Lee, J. H.; Son, H. J.; Choi, Y. K.; Yoon, G. J.; Park, M. H. Synth. Commun. 1996, 26, 83-88. (f) Sepulveda-Arques, J.; Armero-Alarte, T.; Acero-Alarcon, A.; Zaballos-Garcia, E.; Solesio, B. Y.; Carrera, J. E. Tetrahedron 1996, 52, 2097-2102. (g) Williams, L.; Zhang, Z.; Shao, F.; Caroll, F. J.; Joullié, M. M. Tetrahedron 1996, 52, 11673-11694.
18. For other examples related to nucleophilic reactivity of carbamate moieties, see: (a) Agami, C.; Couty, F.; Hamon, L.; Venier, O. Tetrahedron Lett. 1993, 34, 4509-4512. (b) Curran, T. P.; Pollastri, M. P.; Abelleira, S. M.; Messier, R. J.; McCollum, T. A. Tetrahedron Lett. 1994, 35, 5409-5412. (c) Campanini, L.; Duréault, A.; Depezay, J. C. Tetrahedron Lett. 1995, 36, 8015-8018. (d) Vanucci, C.; Brusson, X.; Verdel, V.; Zana, F.; Dhimane, H.; Lhommet, G. Tetrahedron Lett. 1995, 36, 2971-2974. (d) Haddad, M.; Larcheveque, M. Tetrahedron Lett. 1996, 37, 4525-4528. (e) Lee, J. W.; Lee, J. H.; Son, H. J.; Choi, Y. K.; Yoon, G. J.; Park, M. H. Synth. Commun. 1996, 26, 83-88. (f) Sepulveda-Arques, J.; Armero-Alarte, T.; Acero-Alarcon, A.; Zaballos-Garcia, E.; Solesio, B. Y.; Carrera, J. E. Tetrahedron 1996, 52, 2097-2102. (g) Williams, L.; Zhang, Z.; Shao, F.; Caroll, F. J.; Joullié, M. M. Tetrahedron 1996, 52, 11673-11694.
19. For other examples related to nucleophilic reactivity of carbamate moieties, see: (a) Agami, C.; Couty, F.; Hamon, L.; Venier, O. Tetrahedron Lett. 1993, 34, 4509-4512. (b) Curran, T. P.; Pollastri, M. P.; Abelleira, S. M.; Messier, R. J.; McCollum, T. A. Tetrahedron Lett. 1994, 35, 5409-5412. (c) Campanini, L.; Duréault, A.; Depezay, J. C. Tetrahedron Lett. 1995, 36, 8015-8018. (d) Vanucci, C.; Brusson, X.; Verdel, V.; Zana, F.; Dhimane, H.; Lhommet, G. Tetrahedron Lett. 1995, 36, 2971-2974. (d) Haddad, M.; Larcheveque, M. Tetrahedron Lett. 1996, 37, 4525-4528. (e) Lee, J. W.; Lee, J. H.; Son, H. J.; Choi, Y. K.; Yoon, G. J.; Park, M. H. Synth. Commun. 1996, 26, 83-88. (f) Sepulveda-Arques, J.; Armero-Alarte, T.; Acero-Alarcon, A.; Zaballos-Garcia, E.; Solesio, B. Y.; Carrera, J. E. Tetrahedron 1996, 52, 2097-2102. (g) Williams, L.; Zhang, Z.; Shao, F.; Caroll, F. J.; Joullié, M. M. Tetrahedron 1996, 52, 11673-11694.
20. For other examples related to nucleophilic reactivity of carbamate moieties, see: (a) Agami, C.; Couty, F.; Hamon, L.; Venier, O. Tetrahedron Lett. 1993, 34, 4509-4512. (b) Curran, T. P.; Pollastri, M. P.; Abelleira, S. M.; Messier, R. J.; McCollum, T. A. Tetrahedron Lett. 1994, 35, 5409-5412. (c) Campanini, L.; Duréault, A.; Depezay, J. C. Tetrahedron Lett. 1995, 36, 8015-8018. (d) Vanucci, C.; Brusson, X.; Verdel, V.; Zana, F.; Dhimane, H.; Lhommet, G. Tetrahedron Lett. 1995, 36, 2971-2974. (d) Haddad, M.; Larcheveque, M. Tetrahedron Lett. 1996, 37, 4525-4528. (e) Lee, J. W.; Lee, J. H.; Son, H. J.; Choi, Y. K.; Yoon, G. J.; Park, M. H. Synth. Commun. 1996, 26, 83-88. (f) Sepulveda-Arques, J.; Armero-Alarte, T.; Acero-Alarcon, A.; Zaballos-Garcia, E.; Solesio, B. Y.; Carrera, J. E. Tetrahedron 1996, 52, 2097-2102. (g) Williams, L.; Zhang, Z.; Shao, F.; Caroll, F. J.; Joullié, M. M. Tetrahedron 1996, 52, 11673-11694.
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22. For examples of 1,2-stereoinduction in this field, see: (a) Parker, K. A.; O'Fee, R. J. Am. Chem. Soc. 1983, 105, 654-655. (b) Kobayashi, S.; Tashiyuki, I.; Ohno, M. Tetrahedron Lett. 1984, 25, 5079-5082. (c) Kamiyama, K.; Urano, Y.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1987, 28, 3123-3126. (d) Pauls, H. W.; Fraser-Reid, B. J. Am. Chem. Soc. 1980, 102, 3956-3957. (e) Guindon, Y.; Siassi, A.; Ghiro, E.; Bantle, G.; Jung, G. Tetrahedron Lett. 1992, 33, 4257-4260. (f) Guindon, Y.; Slassi, A.; Rancourt, J.; Bantle, G.; Bencheqroun, M.; Murtagh, L.; Ghiro, E.; Jung, G. J. Org. Chem. 1995, 60, 288-289.
23. For examples of 1,2-stereoinduction in this field, see: (a) Parker, K. A.; O'Fee, R. J. Am. Chem. Soc. 1983, 105, 654-655. (b) Kobayashi, S.; Tashiyuki, I.; Ohno, M. Tetrahedron Lett. 1984, 25, 5079-5082. (c) Kamiyama, K.; Urano, Y.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1987, 28, 3123-3126. (d) Pauls, H. W.; Fraser-Reid, B. J. Am. Chem. Soc. 1980, 102, 3956-3957. (e) Guindon, Y.; Siassi, A.; Ghiro, E.; Bantle, G.; Jung, G. Tetrahedron Lett. 1992, 33, 4257-4260. (f) Guindon, Y.; Slassi, A.; Rancourt, J.; Bantle, G.; Bencheqroun, M.; Murtagh, L.; Ghiro, E.; Jung, G. J. Org. Chem. 1995, 60, 288-289.
24. For examples of 1,2-stereoinduction in this field, see: (a) Parker, K. A.; O'Fee, R. J. Am. Chem. Soc. 1983, 105, 654-655. (b) Kobayashi, S.; Tashiyuki, I.; Ohno, M. Tetrahedron Lett. 1984, 25, 5079-5082. (c) Kamiyama, K.; Urano, Y.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1987, 28, 3123-3126. (d) Pauls, H. W.; Fraser-Reid, B. J. Am. Chem. Soc. 1980, 102, 3956-3957. (e) Guindon, Y.; Siassi, A.; Ghiro, E.; Bantle, G.; Jung, G. Tetrahedron Lett. 1992, 33, 4257-4260. (f) Guindon, Y.; Slassi, A.; Rancourt, J.; Bantle, G.; Bencheqroun, M.; Murtagh, L.; Ghiro, E.; Jung, G. J. Org. Chem. 1995, 60, 288-289.
25. For examples of 1,2-stereoinduction in this field, see: (a) Parker, K. A.; O'Fee, R. J. Am. Chem. Soc. 1983, 105, 654-655. (b) Kobayashi, S.; Tashiyuki, I.; Ohno, M. Tetrahedron Lett. 1984, 25, 5079-5082. (c) Kamiyama, K.; Urano, Y.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1987, 28, 3123-3126. (d) Pauls, H. W.; Fraser-Reid, B. J. Am. Chem. Soc. 1980, 102, 3956-3957. (e) Guindon, Y.; Siassi, A.; Ghiro, E.; Bantle, G.; Jung, G. Tetrahedron Lett. 1992, 33, 4257-4260. (f) Guindon, Y.; Slassi, A.; Rancourt, J.; Bantle, G.; Bencheqroun, M.; Murtagh, L.; Ghiro, E.; Jung, G. J. Org. Chem. 1995, 60, 288-289.
26. For examples of 1,2-stereoinduction in this field, see: (a) Parker, K. A.; O'Fee, R. J. Am. Chem. Soc. 1983, 105, 654-655. (b) Kobayashi, S.; Tashiyuki, I.; Ohno, M. Tetrahedron Lett. 1984, 25, 5079-5082. (c) Kamiyama, K.; Urano, Y.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1987, 28, 3123-3126. (d) Pauls, H. W.; Fraser-Reid, B. J. Am. Chem. Soc. 1980, 102, 3956-3957. (e) Guindon, Y.; Siassi, A.; Ghiro, E.; Bantle, G.; Jung, G. Tetrahedron Lett. 1992, 33, 4257-4260. (f) Guindon, Y.; Slassi, A.; Rancourt, J.; Bantle, G.; Bencheqroun, M.; Murtagh, L.; Ghiro, E.; Jung, G. J. Org. Chem. 1995, 60, 288-289.
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38. The isomerization of anti to syn side chain stereoisomer has been described: (a) Gennari, C.; Vulpetti, A.; Donghi, M.; Mongelli, N.; Vanotti, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 1723-1725. (b) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1993, 1375-1376. (c) Gou, D. M.; Liu, Y. C.; Chen, C. S. J. Org. Chem. 1993, 58, 1287-1289. (d) Gennari, C.; Vulpetti, A.; Donghi, M.; Mongelli, N.; Vanotti, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 1723-1725.
39. The isomerization of anti to syn side chain stereoisomer has been described: (a) Gennari, C.; Vulpetti, A.; Donghi, M.; Mongelli, N.; Vanotti, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 1723-1725. (b) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1993, 1375-1376. (c) Gou, D. M.; Liu, Y. C.; Chen, C. S. J. Org. Chem. 1993, 58, 1287-1289. (d) Gennari, C.; Vulpetti, A.; Donghi, M.; Mongelli, N.; Vanotti, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 1723-1725.
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