Catalytic asymmetric carbomagnesiation of unactivated alkenes. A new, effective, active, cheap and recoverable chiral zirconocene

Tetrahedron Letters

Volumn 37, Issue 39, 1996, Pages 7139-7142

  Bell, Louise ^a   Whitby, Richard J ^a   Jones, Raymond V H ^b   Standen, Michael C H ^b  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

METAL COMPLEX; ZIRCONIUM;

ARTICLE; CHIRALITY; DRUG SYNTHESIS;

EID: 0030599242     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01561-4     Document Type: Article

References (41)

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2. 1. Lewis, D. P.; Muller, P. M.; Whitby, R. J.; Jones, R. V. H. Tetrahedron Lett. 1991, 32, 6797. Lewis, D. P.; Whitby, R. J.; Jones, R. V. H. Tetrahedron 1995, 51, 4541.
3. 2. Takahashi, T.; Seki, T.; Nitto, Y.; Sabun, M.; Rousset, C. J.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 6266. Roussel, C. J.; Negishi, E. I.; Suzuki, N.; Takahashi, T. Tetrahedron Lett. 1992, 33, 1965. Hoveyda, A. H.; Xu, Z. M. J. Am. Chem. Soc. 1991, 113, 5079. Houri, A. F.; Didiuk, M. T.; Xu, Z. M.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614. Hoveyda, A. H.; Xu, Z. M.; Morken, J. P.; Houri, A. F. J. Am. Chem. Soc. 1991, 113, 8950; Hoveyda, A. H.; Morken, J. P.; Houri, A. F.; Xu, Z. M. J. Am. Chem. Soc. 1992, 114, 6692; Dzhemilev, U. M.; Sultanov, R. M.; Gaimaldinov, R. G. J. Organomet. Chem. 1995, 491, 1; Dzhemilev, U. M. Tetrahedron 1995, 51, 4333.
4. 2. Takahashi, T.; Seki, T.; Nitto, Y.; Sabun, M.; Rousset, C. J.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 6266. Roussel, C. J.; Negishi, E. I.; Suzuki, N.; Takahashi, T. Tetrahedron Lett. 1992, 33, 1965. Hoveyda, A. H.; Xu, Z. M. J. Am. Chem. Soc. 1991, 113, 5079. Houri, A. F.; Didiuk, M. T.; Xu, Z. M.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614. Hoveyda, A. H.; Xu, Z. M.; Morken, J. P.; Houri, A. F. J. Am. Chem. Soc. 1991, 113, 8950; Hoveyda, A. H.; Morken, J. P.; Houri, A. F.; Xu, Z. M. J. Am. Chem. Soc. 1992, 114, 6692; Dzhemilev, U. M.; Sultanov, R. M.; Gaimaldinov, R. G. J. Organomet. Chem. 1995, 491, 1; Dzhemilev, U. M. Tetrahedron 1995, 51, 4333.
5. 2. Takahashi, T.; Seki, T.; Nitto, Y.; Sabun, M.; Rousset, C. J.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 6266. Roussel, C. J.; Negishi, E. I.; Suzuki, N.; Takahashi, T. Tetrahedron Lett. 1992, 33, 1965. Hoveyda, A. H.; Xu, Z. M. J. Am. Chem. Soc. 1991, 113, 5079. Houri, A. F.; Didiuk, M. T.; Xu, Z. M.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614. Hoveyda, A. H.; Xu, Z. M.; Morken, J. P.; Houri, A. F. J. Am. Chem. Soc. 1991, 113, 8950; Hoveyda, A. H.; Morken, J. P.; Houri, A. F.; Xu, Z. M. J. Am. Chem. Soc. 1992, 114, 6692; Dzhemilev, U. M.; Sultanov, R. M.; Gaimaldinov, R. G. J. Organomet. Chem. 1995, 491, 1; Dzhemilev, U. M. Tetrahedron 1995, 51, 4333.
6. 2. Takahashi, T.; Seki, T.; Nitto, Y.; Sabun, M.; Rousset, C. J.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 6266. Roussel, C. J.; Negishi, E. I.; Suzuki, N.; Takahashi, T. Tetrahedron Lett. 1992, 33, 1965. Hoveyda, A. H.; Xu, Z. M. J. Am. Chem. Soc. 1991, 113, 5079. Houri, A. F.; Didiuk, M. T.; Xu, Z. M.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614. Hoveyda, A. H.; Xu, Z. M.; Morken, J. P.; Houri, A. F. J. Am. Chem. Soc. 1991, 113, 8950; Hoveyda, A. H.; Morken, J. P.; Houri, A. F.; Xu, Z. M. J. Am. Chem. Soc. 1992, 114, 6692; Dzhemilev, U. M.; Sultanov, R. M.; Gaimaldinov, R. G. J. Organomet. Chem. 1995, 491, 1; Dzhemilev, U. M. Tetrahedron 1995, 51, 4333.
7. 2. Takahashi, T.; Seki, T.; Nitto, Y.; Sabun, M.; Rousset, C. J.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 6266. Roussel, C. J.; Negishi, E. I.; Suzuki, N.; Takahashi, T. Tetrahedron Lett. 1992, 33, 1965. Hoveyda, A. H.; Xu, Z. M. J. Am. Chem. Soc. 1991, 113, 5079. Houri, A. F.; Didiuk, M. T.; Xu, Z. M.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614. Hoveyda, A. H.; Xu, Z. M.; Morken, J. P.; Houri, A. F. J. Am. Chem. Soc. 1991, 113, 8950; Hoveyda, A. H.; Morken, J. P.; Houri, A. F.; Xu, Z. M. J. Am. Chem. Soc. 1992, 114, 6692; Dzhemilev, U. M.; Sultanov, R. M.; Gaimaldinov, R. G. J. Organomet. Chem. 1995, 491, 1; Dzhemilev, U. M. Tetrahedron 1995, 51, 4333.
8. 2. Takahashi, T.; Seki, T.; Nitto, Y.; Sabun, M.; Rousset, C. J.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 6266. Roussel, C. J.; Negishi, E. I.; Suzuki, N.; Takahashi, T. Tetrahedron Lett. 1992, 33, 1965. Hoveyda, A. H.; Xu, Z. M. J. Am. Chem. Soc. 1991, 113, 5079. Houri, A. F.; Didiuk, M. T.; Xu, Z. M.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614. Hoveyda, A. H.; Xu, Z. M.; Morken, J. P.; Houri, A. F. J. Am. Chem. Soc. 1991, 113, 8950; Hoveyda, A. H.; Morken, J. P.; Houri, A. F.; Xu, Z. M. J. Am. Chem. Soc. 1992, 114, 6692; Dzhemilev, U. M.; Sultanov, R. M.; Gaimaldinov, R. G. J. Organomet. Chem. 1995, 491, 1; Dzhemilev, U. M. Tetrahedron 1995, 51, 4333.
9. 2. Takahashi, T.; Seki, T.; Nitto, Y.; Sabun, M.; Rousset, C. J.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 6266. Roussel, C. J.; Negishi, E. I.; Suzuki, N.; Takahashi, T. Tetrahedron Lett. 1992, 33, 1965. Hoveyda, A. H.; Xu, Z. M. J. Am. Chem. Soc. 1991, 113, 5079. Houri, A. F.; Didiuk, M. T.; Xu, Z. M.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614. Hoveyda, A. H.; Xu, Z. M.; Morken, J. P.; Houri, A. F. J. Am. Chem. Soc. 1991, 113, 8950; Hoveyda, A. H.; Morken, J. P.; Houri, A. F.; Xu, Z. M. J. Am. Chem. Soc. 1992, 114, 6692; Dzhemilev, U. M.; Sultanov, R. M.; Gaimaldinov, R. G. J. Organomet. Chem. 1995, 491, 1; Dzhemilev, U. M. Tetrahedron 1995, 51, 4333.
10. 2. Takahashi, T.; Seki, T.; Nitto, Y.; Sabun, M.; Rousset, C. J.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 6266. Roussel, C. J.; Negishi, E. I.; Suzuki, N.; Takahashi, T. Tetrahedron Lett. 1992, 33, 1965. Hoveyda, A. H.; Xu, Z. M. J. Am. Chem. Soc. 1991, 113, 5079. Houri, A. F.; Didiuk, M. T.; Xu, Z. M.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614. Hoveyda, A. H.; Xu, Z. M.; Morken, J. P.; Houri, A. F. J. Am. Chem. Soc. 1991, 113, 8950; Hoveyda, A. H.; Morken, J. P.; Houri, A. F.; Xu, Z. M. J. Am. Chem. Soc. 1992, 114, 6692; Dzhemilev, U. M.; Sultanov, R. M.; Gaimaldinov, R. G. J. Organomet. Chem. 1995, 491, 1; Dzhemilev, U. M. Tetrahedron 1995, 51, 4333.
11. 3. Hoveyda, A. H.; Morken, J. P. J. Org. Chem. 1993, 58, 4237.
12. 4. Dzhemilev, U. M.; Vostrikova, O. S.; Sultanov, R. M. Izv. Akad. Nauk SSSR. Ser. Kim. 1983, 218. Dzhemilev, U. M.; Vostrikova, O. S. J. Organomet. Chem. 1985, 255, 43.
13. 4. Dzhemilev, U. M.; Vostrikova, O. S.; Sultanov, R. M. Izv. Akad. Nauk SSSR. Ser. Kim. 1983, 218. Dzhemilev, U. M.; Vostrikova, O. S. J. Organomet. Chem. 1985, 255, 43.
14. 5. Zirconium catalysed inter-and intra-molecular cocyclisation of alkenes with alkyl magnesium or aluminium reagents: Dzhemilev, U. M.; Ibragimov, A. G.; Azhgaliev, M. N.; Muslukhov, R. R. Russ. Chem. Bull. 1994, 43, 255 and references therein; Knight, K. S.; Wang, D.; Waymouth, R. M.; Ziller, J. J. Am. Chem. Soc. 1994, 116, 1845. Uesaka, N.; Mon, M.; Okamura, K.; Date, T. J. Org. Chem. 1994, 59, 4542. Carboalumination of alkenes: Dzhemilev, U. M.; Ibragimov, A. G.; Zolotarev, A. P. Mendeleev Communications 1992, 135; Dzhemilev, U. M.; Ibragimov, A. G. J. Organomet. Chem. 1994, 466, 1. Ethylmagnesiation of conjugated diynes: Takahashi, T.; Aoyagi, K.; Denisov, V.; Suzuki, N.; Choueiry, D.; Negishi, E. Tetrahedron Lett. 1993, 34, 8301. Intramolecular co-cyclisation / elimination of alkenes and allylic ethers: Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575; Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411. Addition / elimination of ethylmagnesium bromide to allylic ethers: Suzuki, N.; Kondakov, D. Y.; Takahashi, T. J. Am. Chem. Soc. 1993, 115, 8485.
15. 5. Zirconium catalysed inter-and intra-molecular cocyclisation of alkenes with alkyl magnesium or aluminium reagents: Dzhemilev, U. M.; Ibragimov, A. G.; Azhgaliev, M. N.; Muslukhov, R. R. Russ. Chem. Bull. 1994, 43, 255 and references therein; Knight, K. S.; Wang, D.; Waymouth, R. M.; Ziller, J. J. Am. Chem. Soc. 1994, 116, 1845. Uesaka, N.; Mon, M.; Okamura, K.; Date, T. J. Org. Chem. 1994, 59, 4542. Carboalumination of alkenes: Dzhemilev, U. M.; Ibragimov, A. G.; Zolotarev, A. P. Mendeleev Communications 1992, 135; Dzhemilev, U. M.; Ibragimov, A. G. J. Organomet. Chem. 1994, 466, 1. Ethylmagnesiation of conjugated diynes: Takahashi, T.; Aoyagi, K.; Denisov, V.; Suzuki, N.; Choueiry, D.; Negishi, E. Tetrahedron Lett. 1993, 34, 8301. Intramolecular co-cyclisation / elimination of alkenes and allylic ethers: Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575; Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411. Addition / elimination of ethylmagnesium bromide to allylic ethers: Suzuki, N.; Kondakov, D. Y.; Takahashi, T. J. Am. Chem. Soc. 1993, 115, 8485.
16. 5. Zirconium catalysed inter-and intra-molecular cocyclisation of alkenes with alkyl magnesium or aluminium reagents: Dzhemilev, U. M.; Ibragimov, A. G.; Azhgaliev, M. N.; Muslukhov, R. R. Russ. Chem. Bull. 1994, 43, 255 and references therein; Knight, K. S.; Wang, D.; Waymouth, R. M.; Ziller, J. J. Am. Chem. Soc. 1994, 116, 1845. Uesaka, N.; Mon, M.; Okamura, K.; Date, T. J. Org. Chem. 1994, 59, 4542. Carboalumination of alkenes: Dzhemilev, U. M.; Ibragimov, A. G.; Zolotarev, A. P. Mendeleev Communications 1992, 135; Dzhemilev, U. M.; Ibragimov, A. G. J. Organomet. Chem. 1994, 466, 1. Ethylmagnesiation of conjugated diynes: Takahashi, T.; Aoyagi, K.; Denisov, V.; Suzuki, N.; Choueiry, D.; Negishi, E. Tetrahedron Lett. 1993, 34, 8301. Intramolecular co-cyclisation / elimination of alkenes and allylic ethers: Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575; Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411. Addition / elimination of ethylmagnesium bromide to allylic ethers: Suzuki, N.; Kondakov, D. Y.; Takahashi, T. J. Am. Chem. Soc. 1993, 115, 8485.
17. 5. Zirconium catalysed inter-and intra-molecular cocyclisation of alkenes with alkyl magnesium or aluminium reagents: Dzhemilev, U. M.; Ibragimov, A. G.; Azhgaliev, M. N.; Muslukhov, R. R. Russ. Chem. Bull. 1994, 43, 255 and references therein; Knight, K. S.; Wang, D.; Waymouth, R. M.; Ziller, J. J. Am. Chem. Soc. 1994, 116, 1845. Uesaka, N.; Mon, M.; Okamura, K.; Date, T. J. Org. Chem. 1994, 59, 4542. Carboalumination of alkenes: Dzhemilev, U. M.; Ibragimov, A. G.; Zolotarev, A. P. Mendeleev Communications 1992, 135; Dzhemilev, U. M.; Ibragimov, A. G. J. Organomet. Chem. 1994, 466, 1. Ethylmagnesiation of conjugated diynes: Takahashi, T.; Aoyagi, K.; Denisov, V.; Suzuki, N.; Choueiry, D.; Negishi, E. Tetrahedron Lett. 1993, 34, 8301. Intramolecular co-cyclisation / elimination of alkenes and allylic ethers: Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575; Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411. Addition / elimination of ethylmagnesium bromide to allylic ethers: Suzuki, N.; Kondakov, D. Y.; Takahashi, T. J. Am. Chem. Soc. 1993, 115, 8485.
18. 5. Zirconium catalysed inter-and intra-molecular cocyclisation of alkenes with alkyl magnesium or aluminium reagents: Dzhemilev, U. M.; Ibragimov, A. G.; Azhgaliev, M. N.; Muslukhov, R. R. Russ. Chem. Bull. 1994, 43, 255 and references therein; Knight, K. S.; Wang, D.; Waymouth, R. M.; Ziller, J. J. Am. Chem. Soc. 1994, 116, 1845. Uesaka, N.; Mon, M.; Okamura, K.; Date, T. J. Org. Chem. 1994, 59, 4542. Carboalumination of alkenes: Dzhemilev, U. M.; Ibragimov, A. G.; Zolotarev, A. P. Mendeleev Communications 1992, 135; Dzhemilev, U. M.; Ibragimov, A. G. J. Organomet. Chem. 1994, 466, 1. Ethylmagnesiation of conjugated diynes: Takahashi, T.; Aoyagi, K.; Denisov, V.; Suzuki, N.; Choueiry, D.; Negishi, E. Tetrahedron Lett. 1993, 34, 8301. Intramolecular co-cyclisation / elimination of alkenes and allylic ethers: Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575; Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411. Addition / elimination of ethylmagnesium bromide to allylic ethers: Suzuki, N.; Kondakov, D. Y.; Takahashi, T. J. Am. Chem. Soc. 1993, 115, 8485.
19. 5. Zirconium catalysed inter-and intra-molecular cocyclisation of alkenes with alkyl magnesium or aluminium reagents: Dzhemilev, U. M.; Ibragimov, A. G.; Azhgaliev, M. N.; Muslukhov, R. R. Russ. Chem. Bull. 1994, 43, 255 and references therein; Knight, K. S.; Wang, D.; Waymouth, R. M.; Ziller, J. J. Am. Chem. Soc. 1994, 116, 1845. Uesaka, N.; Mon, M.; Okamura, K.; Date, T. J. Org. Chem. 1994, 59, 4542. Carboalumination of alkenes: Dzhemilev, U. M.; Ibragimov, A. G.; Zolotarev, A. P. Mendeleev Communications 1992, 135; Dzhemilev, U. M.; Ibragimov, A. G. J. Organomet. Chem. 1994, 466, 1. Ethylmagnesiation of conjugated diynes: Takahashi, T.; Aoyagi, K.; Denisov, V.; Suzuki, N.; Choueiry, D.; Negishi, E. Tetrahedron Lett. 1993, 34, 8301. Intramolecular co-cyclisation / elimination of alkenes and allylic ethers: Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575; Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411. Addition / elimination of ethylmagnesium bromide to allylic ethers: Suzuki, N.; Kondakov, D. Y.; Takahashi, T. J. Am. Chem. Soc. 1993, 115, 8485.
20. 5. Zirconium catalysed inter-and intra-molecular cocyclisation of alkenes with alkyl magnesium or aluminium reagents: Dzhemilev, U. M.; Ibragimov, A. G.; Azhgaliev, M. N.; Muslukhov, R. R. Russ. Chem. Bull. 1994, 43, 255 and references therein; Knight, K. S.; Wang, D.; Waymouth, R. M.; Ziller, J. J. Am. Chem. Soc. 1994, 116, 1845. Uesaka, N.; Mon, M.; Okamura, K.; Date, T. J. Org. Chem. 1994, 59, 4542. Carboalumination of alkenes: Dzhemilev, U. M.; Ibragimov, A. G.; Zolotarev, A. P. Mendeleev Communications 1992, 135; Dzhemilev, U. M.; Ibragimov, A. G. J. Organomet. Chem. 1994, 466, 1. Ethylmagnesiation of conjugated diynes: Takahashi, T.; Aoyagi, K.; Denisov, V.; Suzuki, N.; Choueiry, D.; Negishi, E. Tetrahedron Lett. 1993, 34, 8301. Intramolecular co-cyclisation / elimination of alkenes and allylic ethers: Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575; Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411. Addition / elimination of ethylmagnesium bromide to allylic ethers: Suzuki, N.; Kondakov, D. Y.; Takahashi, T. J. Am. Chem. Soc. 1993, 115, 8485.
21. 5. Zirconium catalysed inter-and intra-molecular cocyclisation of alkenes with alkyl magnesium or aluminium reagents: Dzhemilev, U. M.; Ibragimov, A. G.; Azhgaliev, M. N.; Muslukhov, R. R. Russ. Chem. Bull. 1994, 43, 255 and references therein; Knight, K. S.; Wang, D.; Waymouth, R. M.; Ziller, J. J. Am. Chem. Soc. 1994, 116, 1845. Uesaka, N.; Mon, M.; Okamura, K.; Date, T. J. Org. Chem. 1994, 59, 4542. Carboalumination of alkenes: Dzhemilev, U. M.; Ibragimov, A. G.; Zolotarev, A. P. Mendeleev Communications 1992, 135; Dzhemilev, U. M.; Ibragimov, A. G. J. Organomet. Chem. 1994, 466, 1. Ethylmagnesiation of conjugated diynes: Takahashi, T.; Aoyagi, K.; Denisov, V.; Suzuki, N.; Choueiry, D.; Negishi, E. Tetrahedron Lett. 1993, 34, 8301. Intramolecular co-cyclisation / elimination of alkenes and allylic ethers: Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575; Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411. Addition / elimination of ethylmagnesium bromide to allylic ethers: Suzuki, N.; Kondakov, D. Y.; Takahashi, T. J. Am. Chem. Soc. 1993, 115, 8485.
22. 5. Zirconium catalysed inter-and intra-molecular cocyclisation of alkenes with alkyl magnesium or aluminium reagents: Dzhemilev, U. M.; Ibragimov, A. G.; Azhgaliev, M. N.; Muslukhov, R. R. Russ. Chem. Bull. 1994, 43, 255 and references therein; Knight, K. S.; Wang, D.; Waymouth, R. M.; Ziller, J. J. Am. Chem. Soc. 1994, 116, 1845. Uesaka, N.; Mon, M.; Okamura, K.; Date, T. J. Org. Chem. 1994, 59, 4542. Carboalumination of alkenes: Dzhemilev, U. M.; Ibragimov, A. G.; Zolotarev, A. P. Mendeleev Communications 1992, 135; Dzhemilev, U. M.; Ibragimov, A. G. J. Organomet. Chem. 1994, 466, 1. Ethylmagnesiation of conjugated diynes: Takahashi, T.; Aoyagi, K.; Denisov, V.; Suzuki, N.; Choueiry, D.; Negishi, E. Tetrahedron Lett. 1993, 34, 8301. Intramolecular co-cyclisation / elimination of alkenes and allylic ethers: Knight, K. S.; Waymouth, R. M. Organometallics 1994, 13, 2575; Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Organometallics 1994, 13, 3411. Addition / elimination of ethylmagnesium bromide to allylic ethers: Suzuki, N.; Kondakov, D. Y.; Takahashi, T. J. Am. Chem. Soc. 1993, 115, 8485.
23. 6. Asymmetric addition / elimination of ethylmagnesium bromide to allylic ethers using 1: Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997. Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1994, 116, 3123; Visser, M. S.; Harrity, J. P. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 3779.
24. 6. Asymmetric addition / elimination of ethylmagnesium bromide to allylic ethers using 1: Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997. Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1994, 116, 3123; Visser, M. S.; Harrity, J. P. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 3779.
25. 6. Asymmetric addition / elimination of ethylmagnesium bromide to allylic ethers using 1: Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997. Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1994, 116, 3123; Visser, M. S.; Harrity, J. P. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 3779.
26. 7. Visser, M. S.; Hoveyda, A. H. Tetrahedron 1995, 51, 4383.
27. 8. Coates, G. W.; Waymouth, R. M. J. Am. Chem. Soc. 1993, 115, 91; Jaquith, J. B.; Guan, J. Y.; Wang, S. T.; Collins, S. Organometallics 1995, 14, 1079; Grossman, R. B.; Davis, W. M.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 2321; Gately, D. A.; Norton, J. R. J. Am. Chem. Soc. 1996,118, 3479; Halterman, R. L. Chem. Rev. 1992, 92, 965. An improved route for the synthesis of 1 was recently reported: Diamond, G. M.; Rodewald, S.; Jordan, R. F. Organometallics 1995, 14, 5.
28. 8. Coates, G. W.; Waymouth, R. M. J. Am. Chem. Soc. 1993, 115, 91; Jaquith, J. B.; Guan, J. Y.; Wang, S. T.; Collins, S. Organometallics 1995, 14, 1079; Grossman, R. B.; Davis, W. M.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 2321; Gately, D. A.; Norton, J. R. J. Am. Chem. Soc. 1996,118, 3479; Halterman, R. L. Chem. Rev. 1992, 92, 965. An improved route for the synthesis of 1 was recently reported: Diamond, G. M.; Rodewald, S.; Jordan, R. F. Organometallics 1995, 14, 5.
29. 8. Coates, G. W.; Waymouth, R. M. J. Am. Chem. Soc. 1993, 115, 91; Jaquith, J. B.; Guan, J. Y.; Wang, S. T.; Collins, S. Organometallics 1995, 14, 1079; Grossman, R. B.; Davis, W. M.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 2321; Gately, D. A.; Norton, J. R. J. Am. Chem. Soc. 1996,118, 3479; Halterman, R. L. Chem. Rev. 1992, 92, 965. An improved route for the synthesis of 1 was recently reported: Diamond, G. M.; Rodewald, S.; Jordan, R. F. Organometallics 1995, 14, 5.
30. 8. Coates, G. W.; Waymouth, R. M. J. Am. Chem. Soc. 1993, 115, 91; Jaquith, J. B.; Guan, J. Y.; Wang, S. T.; Collins, S. Organometallics 1995, 14, 1079; Grossman, R. B.; Davis, W. M.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 2321; Gately, D. A.; Norton, J. R. J. Am. Chem. Soc. 1996,118, 3479; Halterman, R. L. Chem. Rev. 1992, 92, 965. An improved route for the synthesis of 1 was recently reported: Diamond, G. M.; Rodewald, S.; Jordan, R. F. Organometallics 1995, 14, 5.
31. 8. Coates, G. W.; Waymouth, R. M. J. Am. Chem. Soc. 1993, 115, 91; Jaquith, J. B.; Guan, J. Y.; Wang, S. T.; Collins, S. Organometallics 1995, 14, 1079; Grossman, R. B.; Davis, W. M.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 2321; Gately, D. A.; Norton, J. R. J. Am. Chem. Soc. 1996,118, 3479; Halterman, R. L. Chem. Rev. 1992, 92, 965. An improved route for the synthesis of 1 was recently reported: Diamond, G. M.; Rodewald, S.; Jordan, R. F. Organometallics 1995, 14, 5.
32. 8. Coates, G. W.; Waymouth, R. M. J. Am. Chem. Soc. 1993, 115, 91; Jaquith, J. B.; Guan, J. Y.; Wang, S. T.; Collins, S. Organometallics 1995, 14, 1079; Grossman, R. B.; Davis, W. M.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 2321; Gately, D. A.; Norton, J. R. J. Am. Chem. Soc. 1996,118, 3479; Halterman, R. L. Chem. Rev. 1992, 92, 965. An improved route for the synthesis of 1 was recently reported: Diamond, G. M.; Rodewald, S.; Jordan, R. F. Organometallics 1995, 14, 5.
33. 9. Wild, F. R. W. P.; Wasiucionek, M.; Huttner, G., Brintzinger, H. H. J. Organomet. Chem. 1985, 288, 63; Schafer, A.; Karl, E.; Zsolnai, L.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1987, 328, 87.
34. 9. Wild, F. R. W. P.; Wasiucionek, M.; Huttner, G., Brintzinger, H. H. J. Organomet. Chem. 1985, 288, 63; Schafer, A.; Karl, E.; Zsolnai, L.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1987, 328, 87.
35. 10. Grossman, R. B.; Doyle, R. A.; Buchwald, S. L. Organometallics 1991, 10, 1501.
36. 11. Hoveyda (ref. 3) has used 1 for the carbomagnesiation of chiral terminal alkenes with an allylic hydroxy or ether group. The d.e.'s reported show that the diastereocontrol is dominated by the chirality of the hydroxy/ether group, but the additional influence of the catalyst chirality (matched / mismatched pairs) is consistent with our reported 26-27% e.e's:
37. 12. All new compounds were fully characterised. All yields refer to pure isolated products.
38. 2, but under conditions which favour a different mechanism (direct insertion of the alkene into a cationic ethyl zirconocene). Under conditions which favour the same mechanism to herein he obtains low conversions and around 30% e.e.'s consistent with our results: Kondakov, D. Y.; Negishi, E. J. Am. Chem. Soc. 1996, 118, 1577.
39. 14. Erker, G.; Aulbach, M.; Knickmeier, M.; Wingbermühle, D.; Krüger, C.; Nolte, M.; Werner, S. J. Am. Chem. Soc. 1993, 115, 4590.
40. 15. Lund, E. C.; Livinghouse, T. Organometallics 1990, 9, 2426.
41. 16. International Patent Application no. PCT/GB96/00264. X-Ray structure of ent-5 determined by Dr. C. Ceccarelli, Zeneca Pharmaceuticals, Wilmington, Dellaware, U.S.A. Full details will be reported shortly.