Stereoselective chelate-controlled addition of Grignard reagents to unsaturated medium-ring heterocycles

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 854-860

  Adams, Jeffrey A ^a   Heron, Nicola M ^a   Koss, Ann Marie ^a   Hoveyda, Amir H ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; HETEROCYCLIC COMPOUND; ORGANOMETALLIC COMPOUND; REAGENT; ZIRCONIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHELATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; KINETICS; ORGANIC CHEMISTRY; STEREOCHEMISTRY;

EID: 0033525177     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981745e     Document Type: Article

References (36)

1. For uncatalyzed examples of the addition of Grignard reagents to olefins, see: (a) Eisch, J. J. J. Organomet. Chem. 1980, 200, 101-117 and references therein. (b) Felkin, H.; Kaeseberg, C. Tetrahedron Lett. 1970, 4587-4590 and references therein. (c) Richey, H. G.; Domalski, M. S. J. Org. Chem. 1981, 46, 3780-3783 and references therein. (d) Swiss, K. A.; Liotta, D. C.; Maryanoff, C. A. J. Am. Chem. Soc. 1990, 112, 9393-9394 and references therein.
2. For uncatalyzed examples of the addition of Grignard reagents to olefins, see: (a) Eisch, J. J. J. Organomet. Chem. 1980, 200, 101- 117 and references therein. (b) Felkin, H.; Kaeseberg, C. Tetrahedron Lett. 1970, 4587-4590 and references therein. (c) Richey, H. G.; Domalski, M. S. J. Org. Chem. 1981, 46, 3780-3783 and references therein. (d) Swiss, K. A.; Liotta, D. C.; Maryanoff, C. A. J. Am. Chem. Soc. 1990, 112, 9393-9394 and references therein.
3. For uncatalyzed examples of the addition of Grignard reagents to olefins, see: (a) Eisch, J. J. J. Organomet. Chem. 1980, 200, 101- 117 and references therein. (b) Felkin, H.; Kaeseberg, C. Tetrahedron Lett. 1970, 4587-4590 and references therein. (c) Richey, H. G.; Domalski, M. S. J. Org. Chem. 1981, 46, 3780-3783 and references therein. (d) Swiss, K. A.; Liotta, D. C.; Maryanoff, C. A. J. Am. Chem. Soc. 1990, 112, 9393-9394 and references therein.
4. For uncatalyzed examples of the addition of Grignard reagents to olefins, see: (a) Eisch, J. J. J. Organomet. Chem. 1980, 200, 101- 117 and references therein. (b) Felkin, H.; Kaeseberg, C. Tetrahedron Lett. 1970, 4587-4590 and references therein. (c) Richey, H. G.; Domalski, M. S. J. Org. Chem. 1981, 46, 3780-3783 and references therein. (d) Swiss, K. A.; Liotta, D. C.; Maryanoff, C. A. J. Am. Chem. Soc. 1990, 112, 9393-9394 and references therein.
5. For Zr-catalyzed diastereoselective additions: (a) Houri, A. F.; Didiuk, M. T.; Xu, Z.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614-6624. (b) Morken, J. P.; Hoveyda, A. H. J. Org. Chem. 1993, 58, 4237-4244. For Zr-catalyzed enantioselective additions: (c) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6697-6698. (d) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097-7104. Zr-catalyzed kinetic resolution through enantioselective allylic ether alkylation: (e) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1994, 116, 3123-3124. (f) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298. (g) Visser, M. S.; Harrity, J. P. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 3779-3780. (h) Harrity, J. P. A.; La, D. S.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 2343-2351.
6. For Zr-catalyzed diastereoselective additions: (a) Houri, A. F.; Didiuk, M. T.; Xu, Z.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614-6624. (b) Morken, J. P.; Hoveyda, A. H. J. Org. Chem. 1993, 58, 4237-4244. For Zr-catalyzed enantioselective additions: (c) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6697-6698. (d) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097-7104. Zr-catalyzed kinetic resolution through enantioselective allylic ether alkylation: (e) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1994, 116, 3123-3124. (f) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298. (g) Visser, M. S.; Harrity, J. P. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 3779-3780. (h) Harrity, J. P. A.; La, D. S.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 2343-2351.
7. For Zr-catalyzed diastereoselective additions: (a) Houri, A. F.; Didiuk, M. T.; Xu, Z.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614-6624. (b) Morken, J. P.; Hoveyda, A. H. J. Org. Chem. 1993, 58, 4237-4244. For Zr-catalyzed enantioselective additions: (c) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6697-6698. (d) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097-7104. Zr-catalyzed kinetic resolution through enantioselective allylic ether alkylation: (e) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1994, 116, 3123-3124. (f) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298. (g) Visser, M. S.; Harrity, J. P. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 3779-3780. (h) Harrity, J. P. A.; La, D. S.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 2343-2351.
8. For Zr-catalyzed diastereoselective additions: (a) Houri, A. F.; Didiuk, M. T.; Xu, Z.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614-6624. (b) Morken, J. P.; Hoveyda, A. H. J. Org. Chem. 1993, 58, 4237-4244. For Zr-catalyzed enantioselective additions: (c) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6697-6698. (d) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097-7104. Zr-catalyzed kinetic resolution through enantioselective allylic ether alkylation: (e) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1994, 116, 3123-3124. (f) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298. (g) Visser, M. S.; Harrity, J. P. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 3779-3780. (h) Harrity, J. P. A.; La, D. S.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 2343-2351.
9. For Zr-catalyzed diastereoselective additions: (a) Houri, A. F.; Didiuk, M. T.; Xu, Z.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614-6624. (b) Morken, J. P.; Hoveyda, A. H. J. Org. Chem. 1993, 58, 4237-4244. For Zr-catalyzed enantioselective additions: (c) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6697-6698. (d) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097-7104. Zr-catalyzed kinetic resolution through enantioselective allylic ether alkylation: (e) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1994, 116, 3123-3124. (f) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298. (g) Visser, M. S.; Harrity, J. P. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 3779-3780. (h) Harrity, J. P. A.; La, D. S.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 2343-2351.
10. For Zr-catalyzed diastereoselective additions: (a) Houri, A. F.; Didiuk, M. T.; Xu, Z.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614-6624. (b) Morken, J. P.; Hoveyda, A. H. J. Org. Chem. 1993, 58, 4237-4244. For Zr-catalyzed enantioselective additions: (c) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6697-6698. (d) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097-7104. Zr-catalyzed kinetic resolution through enantioselective allylic ether alkylation: (e) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1994, 116, 3123-3124. (f) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298. (g) Visser, M. S.; Harrity, J. P. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 3779-3780. (h) Harrity, J. P. A.; La, D. S.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 2343-2351.
11. For Zr-catalyzed diastereoselective additions: (a) Houri, A. F.; Didiuk, M. T.; Xu, Z.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614-6624. (b) Morken, J. P.; Hoveyda, A. H. J. Org. Chem. 1993, 58, 4237-4244. For Zr-catalyzed enantioselective additions: (c) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6697-6698. (d) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097-7104. Zr-catalyzed kinetic resolution through enantioselective allylic ether alkylation: (e) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1994, 116, 3123-3124. (f) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298. (g) Visser, M. S.; Harrity, J. P. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 3779-3780. (h) Harrity, J. P. A.; La, D. S.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 2343-2351.
12. For Zr-catalyzed diastereoselective additions: (a) Houri, A. F.; Didiuk, M. T.; Xu, Z.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614-6624. (b) Morken, J. P.; Hoveyda, A. H. J. Org. Chem. 1993, 58, 4237-4244. For Zr-catalyzed enantioselective additions: (c) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6697-6698. (d) Didiuk, M. T.; Johannes, C. W.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7097-7104. Zr-catalyzed kinetic resolution through enantioselective allylic ether alkylation: (e) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1994, 116, 3123-3124. (f) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298. (g) Visser, M. S.; Harrity, J. P. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 3779-3780. (h) Harrity, J. P. A.; La, D. S.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 2343-2351.
13. For an example of a Cu-catalyzed addition of Grignard reagents to allylic ethers, see: (a) Gendreau, Y.; Normant, J. F. Tetrahedron 1979, 35, 1517-1521. For related Ni-catalyzed processes, see: (b) Consiglio, G.; Piccolo, O.; Roncetti, L.; Morandini, F. Tetrahedron 1986, 42, 2043-2053. (c) Didiuk, M. T.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7273-7274. For an excellent recent review, see: (d) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257- 276.
14. For an example of a Cu-catalyzed addition of Grignard reagents to allylic ethers, see: (a) Gendreau, Y.; Normant, J. F. Tetrahedron 1979, 35, 1517-1521. For related Ni-catalyzed processes, see: (b) Consiglio, G.; Piccolo, O.; Roncetti, L.; Morandini, F. Tetrahedron 1986, 42, 2043-2053. (c) Didiuk, M. T.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7273-7274. For an excellent recent review, see: (d) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257- 276.
15. For an example of a Cu-catalyzed addition of Grignard reagents to allylic ethers, see: (a) Gendreau, Y.; Normant, J. F. Tetrahedron 1979, 35, 1517-1521. For related Ni-catalyzed processes, see: (b) Consiglio, G.; Piccolo, O.; Roncetti, L.; Morandini, F. Tetrahedron 1986, 42, 2043-2053. (c) Didiuk, M. T.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7273-7274. For an excellent recent review, see: (d) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257- 276.
16. For an example of a Cu-catalyzed addition of Grignard reagents to allylic ethers, see: (a) Gendreau, Y.; Normant, J. F. Tetrahedron 1979, 35, 1517-1521. For related Ni-catalyzed processes, see: (b) Consiglio, G.; Piccolo, O.; Roncetti, L.; Morandini, F. Tetrahedron 1986, 42, 2043-2053. (c) Didiuk, M. T.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7273-7274. For an excellent recent review, see: (d) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276.
17. For a review of directed reactions, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
18. Heron, N. M.; Adams, J. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 6205-6206.
19. For recent reviews on the utility of olefin metathesis in organic synthesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452 and references therein. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833-1836 and references therein. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (d) Furstner, A. Topics Catal. 1997, 4, 285- 299. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans 1 1998, 371- 388. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
20. For recent reviews on the utility of olefin metathesis in organic synthesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452 and references therein. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833-1836 and references therein. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (d) Furstner, A. Topics Catal. 1997, 4, 285- 299. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans 1 1998, 371- 388. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
21. For recent reviews on the utility of olefin metathesis in organic synthesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452 and references therein. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833-1836 and references therein. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (d) Furstner, A. Topics Catal. 1997, 4, 285- 299. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans 1 1998, 371- 388. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
22. For recent reviews on the utility of olefin metathesis in organic synthesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452 and references therein. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833-1836 and references therein. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (d) Furstner, A. Topics Catal. 1997, 4, 285-299. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans 1 1998, 371- 388. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
23. For recent reviews on the utility of olefin metathesis in organic synthesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452 and references therein. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833-1836 and references therein. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (d) Furstner, A. Topics Catal. 1997, 4, 285- 299. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans 1 1998, 371-388. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
24. For recent reviews on the utility of olefin metathesis in organic synthesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452 and references therein. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833-1836 and references therein. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056. (d) Furstner, A. Topics Catal. 1997, 4, 285- 299. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans 1 1998, 371- 388. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
25. Relative rates were calculated by an equation reported previously: (a) Balavoine, G.; Moradpour, A.; Kagan, H. B. J. Am. Chem. Soc. 1974, 96, 5152-5158. (b) Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237-6240.
26. Relative rates were calculated by an equation reported previously: (a) Balavoine, G.; Moradpour, A.; Kagan, H. B. J. Am. Chem. Soc. 1974, 96, 5152-5158. (b) Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237-6240.
27. In our initial report (ref 5), seven-membered ring substrates were proposed to react through a pseudo-chair conformer. However, closer inspection of models indicates that the related pseudo-boat conformers carry less torsional strain.
28. Chin, B.; Buchwald, S. L. J. Org. Chem. 1996, 67, 5650-5651. Control experiments show that binol and biphen derivatives of the chiral Zr catalyst afford identical results in asymmetric carbomagnesation reactions.
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34. (b) La, D. S.; Alexander, J. A.; Cefalo, D. R.; Graff, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720-9721.
35. Grossman, R. B.; Davis, W. M.; Buchwald, S. L. J. Am. Chem. Soc. 1981, 113, 2321-2322 and references therein.
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