Enantioselective carbolithiation of cinnamyl acetals. New access to chiral disubstituted cyclopropanes

Journal of Organic Chemistry

Volumn 62, Issue 15, 1997, Pages 4898-4899

  Norsikian, Stephanie ^a   Marek, Ilane ^a   Poisson, Jean François ^a   Normant, Jean F ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CINNAMYL ALCOHOL; CYCLOPROPANE; LITHIUM;

ARTICLE; CATALYSIS; CHELATION; CHIRALITY; ENANTIOMER; POLYMERIZATION; STEREOCHEMISTRY;

EID: 0030743259     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9705172     Document Type: Article

References (59)

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17. Asymmetric carbocupration of cyclopropene: (a) Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1990, 112, 7428. Asymmetric allylzincation of cyclopropene: (b) Kubota, K.; Nakamura, M.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5879. (c) Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179. Zirconium-catalyzed asymmetric ethylmagnesiation: (d) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997. (e) Hoveyda, A. H.; Morken, J. P. J. Org. Chem. 1993, 58, 4237. (f) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 116, 3123. (g) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291. (h) Bell, L.; Whitby, R. J.; Jones, R. V. H., Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. Zirconium-catalyzed asymmetric alkylalumination: (i) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1995, 117, 10771. (j) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1996, 118, 1577. Asymmetric ring opening of an oxabicyclic compound: (k) Lautens, M.; Gajda, C.; Chiu, P. J. Chem. Soc., Chem. Commun. 1993, 1193. Intramolecular carbolithiation: (l) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322. (m) Krief, A.; Bousbaa, J. Synlett 1996, 1007. (n) Asymmetric carbometalation of zincated hydrazones to cyclopropene: Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792.
18. Asymmetric carbocupration of cyclopropene: (a) Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1990, 112, 7428. Asymmetric allylzincation of cyclopropene: (b) Kubota, K.; Nakamura, M.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5879. (c) Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179. Zirconium-catalyzed asymmetric ethylmagnesiation: (d) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997. (e) Hoveyda, A. H.; Morken, J. P. J. Org. Chem. 1993, 58, 4237. (f) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 116, 3123. (g) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291. (h) Bell, L.; Whitby, R. J.; Jones, R. V. H., Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. Zirconium-catalyzed asymmetric alkylalumination: (i) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1995, 117, 10771. (j) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1996, 118, 1577. Asymmetric ring opening of an oxabicyclic compound: (k) Lautens, M.; Gajda, C.; Chiu, P. J. Chem. Soc., Chem. Commun. 1993, 1193. Intramolecular carbolithiation: (l) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322. (m) Krief, A.; Bousbaa, J. Synlett 1996, 1007. (n) Asymmetric carbometalation of zincated hydrazones to cyclopropene: Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792.
19. Asymmetric carbocupration of cyclopropene: (a) Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1990, 112, 7428. Asymmetric allylzincation of cyclopropene: (b) Kubota, K.; Nakamura, M.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5879. (c) Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179. Zirconium-catalyzed asymmetric ethylmagnesiation: (d) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997. (e) Hoveyda, A. H.; Morken, J. P. J. Org. Chem. 1993, 58, 4237. (f) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 116, 3123. (g) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291. (h) Bell, L.; Whitby, R. J.; Jones, R. V. H., Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. Zirconium-catalyzed asymmetric alkylalumination: (i) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1995, 117, 10771. (j) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1996, 118, 1577. Asymmetric ring opening of an oxabicyclic compound: (k) Lautens, M.; Gajda, C.; Chiu, P. J. Chem. Soc., Chem. Commun. 1993, 1193. Intramolecular carbolithiation: (l) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322. (m) Krief, A.; Bousbaa, J. Synlett 1996, 1007. (n) Asymmetric carbometalation of zincated hydrazones to cyclopropene: Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792.
20. Asymmetric carbocupration of cyclopropene: (a) Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1990, 112, 7428. Asymmetric allylzincation of cyclopropene: (b) Kubota, K.; Nakamura, M.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5879. (c) Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179. Zirconium-catalyzed asymmetric ethylmagnesiation: (d) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997. (e) Hoveyda, A. H.; Morken, J. P. J. Org. Chem. 1993, 58, 4237. (f) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 116, 3123. (g) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291. (h) Bell, L.; Whitby, R. J.; Jones, R. V. H., Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. Zirconium-catalyzed asymmetric alkylalumination: (i) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1995, 117, 10771. (j) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1996, 118, 1577. Asymmetric ring opening of an oxabicyclic compound: (k) Lautens, M.; Gajda, C.; Chiu, P. J. Chem. Soc., Chem. Commun. 1993, 1193. Intramolecular carbolithiation: (l) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322. (m) Krief, A.; Bousbaa, J. Synlett 1996, 1007. (n) Asymmetric carbometalation of zincated hydrazones to cyclopropene: Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792.
21. Asymmetric carbocupration of cyclopropene: (a) Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1990, 112, 7428. Asymmetric allylzincation of cyclopropene: (b) Kubota, K.; Nakamura, M.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5879. (c) Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179. Zirconium-catalyzed asymmetric ethylmagnesiation: (d) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997. (e) Hoveyda, A. H.; Morken, J. P. J. Org. Chem. 1993, 58, 4237. (f) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 116, 3123. (g) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291. (h) Bell, L.; Whitby, R. J.; Jones, R. V. H., Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. Zirconium-catalyzed asymmetric alkylalumination: (i) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1995, 117, 10771. (j) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1996, 118, 1577. Asymmetric ring opening of an oxabicyclic compound: (k) Lautens, M.; Gajda, C.; Chiu, P. J. Chem. Soc., Chem. Commun. 1993, 1193. Intramolecular carbolithiation: (l) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322. (m) Krief, A.; Bousbaa, J. Synlett 1996, 1007. (n) Asymmetric carbometalation of zincated hydrazones to cyclopropene: Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792.
22. Asymmetric carbocupration of cyclopropene: (a) Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1990, 112, 7428. Asymmetric allylzincation of cyclopropene: (b) Kubota, K.; Nakamura, M.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5879. (c) Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179. Zirconium-catalyzed asymmetric ethylmagnesiation: (d) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997. (e) Hoveyda, A. H.; Morken, J. P. J. Org. Chem. 1993, 58, 4237. (f) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 116, 3123. (g) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291. (h) Bell, L.; Whitby, R. J.; Jones, R. V. H., Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. Zirconium-catalyzed asymmetric alkylalumination: (i) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1995, 117, 10771. (j) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1996, 118, 1577. Asymmetric ring opening of an oxabicyclic compound: (k) Lautens, M.; Gajda, C.; Chiu, P. J. Chem. Soc., Chem. Commun. 1993, 1193. Intramolecular carbolithiation: (l) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322. (m) Krief, A.; Bousbaa, J. Synlett 1996, 1007. (n) Asymmetric carbometalation of zincated hydrazones to cyclopropene: Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792.
23. Asymmetric carbocupration of cyclopropene: (a) Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1990, 112, 7428. Asymmetric allylzincation of cyclopropene: (b) Kubota, K.; Nakamura, M.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5879. (c) Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179. Zirconium-catalyzed asymmetric ethylmagnesiation: (d) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997. (e) Hoveyda, A. H.; Morken, J. P. J. Org. Chem. 1993, 58, 4237. (f) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 116, 3123. (g) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291. (h) Bell, L.; Whitby, R. J.; Jones, R. V. H., Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. Zirconium-catalyzed asymmetric alkylalumination: (i) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1995, 117, 10771. (j) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1996, 118, 1577. Asymmetric ring opening of an oxabicyclic compound: (k) Lautens, M.; Gajda, C.; Chiu, P. J. Chem. Soc., Chem. Commun. 1993, 1193. Intramolecular carbolithiation: (l) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322. (m) Krief, A.; Bousbaa, J. Synlett 1996, 1007. (n) Asymmetric carbometalation of zincated hydrazones to cyclopropene: Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792.
24. Asymmetric carbocupration of cyclopropene: (a) Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1990, 112, 7428. Asymmetric allylzincation of cyclopropene: (b) Kubota, K.; Nakamura, M.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5879. (c) Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179. Zirconium-catalyzed asymmetric ethylmagnesiation: (d) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997. (e) Hoveyda, A. H.; Morken, J. P. J. Org. Chem. 1993, 58, 4237. (f) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 116, 3123. (g) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291. (h) Bell, L.; Whitby, R. J.; Jones, R. V. H., Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. Zirconium-catalyzed asymmetric alkylalumination: (i) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1995, 117, 10771. (j) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1996, 118, 1577. Asymmetric ring opening of an oxabicyclic compound: (k) Lautens, M.; Gajda, C.; Chiu, P. J. Chem. Soc., Chem. Commun. 1993, 1193. Intramolecular carbolithiation: (l) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322. (m) Krief, A.; Bousbaa, J. Synlett 1996, 1007. (n) Asymmetric carbometalation of zincated hydrazones to cyclopropene: Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792.
25. Asymmetric carbocupration of cyclopropene: (a) Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1990, 112, 7428. Asymmetric allylzincation of cyclopropene: (b) Kubota, K.; Nakamura, M.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5879. (c) Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179. Zirconium-catalyzed asymmetric ethylmagnesiation: (d) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997. (e) Hoveyda, A. H.; Morken, J. P. J. Org. Chem. 1993, 58, 4237. (f) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 116, 3123. (g) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291. (h) Bell, L.; Whitby, R. J.; Jones, R. V. H., Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. Zirconium-catalyzed asymmetric alkylalumination: (i) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1995, 117, 10771. (j) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1996, 118, 1577. Asymmetric ring opening of an oxabicyclic compound: (k) Lautens, M.; Gajda, C.; Chiu, P. J. Chem. Soc., Chem. Commun. 1993, 1193. Intramolecular carbolithiation: (l) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322. (m) Krief, A.; Bousbaa, J. Synlett 1996, 1007. (n) Asymmetric carbometalation of zincated hydrazones to cyclopropene: Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792.
26. Asymmetric carbocupration of cyclopropene: (a) Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1990, 112, 7428. Asymmetric allylzincation of cyclopropene: (b) Kubota, K.; Nakamura, M.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5879. (c) Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179. Zirconium-catalyzed asymmetric ethylmagnesiation: (d) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997. (e) Hoveyda, A. H.; Morken, J. P. J. Org. Chem. 1993, 58, 4237. (f) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 116, 3123. (g) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291. (h) Bell, L.; Whitby, R. J.; Jones, R. V. H., Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. Zirconium-catalyzed asymmetric alkylalumination: (i) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1995, 117, 10771. (j) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1996, 118, 1577. Asymmetric ring opening of an oxabicyclic compound: (k) Lautens, M.; Gajda, C.; Chiu, P. J. Chem. Soc., Chem. Commun. 1993, 1193. Intramolecular carbolithiation: (l) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322. (m) Krief, A.; Bousbaa, J. Synlett 1996, 1007. (n) Asymmetric carbometalation of zincated hydrazones to cyclopropene: Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792.
27. Asymmetric carbocupration of cyclopropene: (a) Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1990, 112, 7428. Asymmetric allylzincation of cyclopropene: (b) Kubota, K.; Nakamura, M.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5879. (c) Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179. Zirconium-catalyzed asymmetric ethylmagnesiation: (d) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997. (e) Hoveyda, A. H.; Morken, J. P. J. Org. Chem. 1993, 58, 4237. (f) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 116, 3123. (g) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291. (h) Bell, L.; Whitby, R. J.; Jones, R. V. H., Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. Zirconium-catalyzed asymmetric alkylalumination: (i) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1995, 117, 10771. (j) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1996, 118, 1577. Asymmetric ring opening of an oxabicyclic compound: (k) Lautens, M.; Gajda, C.; Chiu, P. J. Chem. Soc., Chem. Commun. 1993, 1193. Intramolecular carbolithiation: (l) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322. (m) Krief, A.; Bousbaa, J. Synlett 1996, 1007. (n) Asymmetric carbometalation of zincated hydrazones to cyclopropene: Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792.
28. Asymmetric carbocupration of cyclopropene: (a) Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1990, 112, 7428. Asymmetric allylzincation of cyclopropene: (b) Kubota, K.; Nakamura, M.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5879. (c) Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179. Zirconium-catalyzed asymmetric ethylmagnesiation: (d) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997. (e) Hoveyda, A. H.; Morken, J. P. J. Org. Chem. 1993, 58, 4237. (f) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 116, 3123. (g) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291. (h) Bell, L.; Whitby, R. J.; Jones, R. V. H., Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. Zirconium-catalyzed asymmetric alkylalumination: (i) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1995, 117, 10771. (j) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1996, 118, 1577. Asymmetric ring opening of an oxabicyclic compound: (k) Lautens, M.; Gajda, C.; Chiu, P. J. Chem. Soc., Chem. Commun. 1993, 1193. Intramolecular carbolithiation: (l) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322. (m) Krief, A.; Bousbaa, J. Synlett 1996, 1007. (n) Asymmetric carbometalation of zincated hydrazones to cyclopropene: Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792.
29. Asymmetric carbocupration of cyclopropene: (a) Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1990, 112, 7428. Asymmetric allylzincation of cyclopropene: (b) Kubota, K.; Nakamura, M.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5879. (c) Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179. Zirconium-catalyzed asymmetric ethylmagnesiation: (d) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997. (e) Hoveyda, A. H.; Morken, J. P. J. Org. Chem. 1993, 58, 4237. (f) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 116, 3123. (g) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291. (h) Bell, L.; Whitby, R. J.; Jones, R. V. H., Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. Zirconium-catalyzed asymmetric alkylalumination: (i) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1995, 117, 10771. (j) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1996, 118, 1577. Asymmetric ring opening of an oxabicyclic compound: (k) Lautens, M.; Gajda, C.; Chiu, P. J. Chem. Soc., Chem. Commun. 1993, 1193. Intramolecular carbolithiation: (l) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322. (m) Krief, A.; Bousbaa, J. Synlett 1996, 1007. (n) Asymmetric carbometalation of zincated hydrazones to cyclopropene: Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792.
30. Asymmetric carbocupration of cyclopropene: (a) Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1990, 112, 7428. Asymmetric allylzincation of cyclopropene: (b) Kubota, K.; Nakamura, M.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5879. (c) Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179. Zirconium-catalyzed asymmetric ethylmagnesiation: (d) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6997. (e) Hoveyda, A. H.; Morken, J. P. J. Org. Chem. 1993, 58, 4237. (f) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 116, 3123. (g) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291. (h) Bell, L.; Whitby, R. J.; Jones, R. V. H., Standen, M. C. H. Tetrahedron Lett. 1996, 37, 7139. Zirconium-catalyzed asymmetric alkylalumination: (i) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1995, 117, 10771. (j) Kondakov, D. Y.; Neghishi, E. I. J. Am. Chem. Soc. 1996, 118, 1577. Asymmetric ring opening of an oxabicyclic compound: (k) Lautens, M.; Gajda, C.; Chiu, P. J. Chem. Soc., Chem. Commun. 1993, 1193. Intramolecular carbolithiation: (l) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322. (m) Krief, A.; Bousbaa, J. Synlett 1996, 1007. (n) Asymmetric carbometalation of zincated hydrazones to cyclopropene: Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792.
31. Klein, S.; Marek, I.; Poissson, J. F.; Normant, J. F. J. Am. Chem. Soc. 1995, 117, 8853.
32. The synthesis and the enantioselectivities of these different ligands will be reported in due course.
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41. For a recent review on the use of (-)-sparteine in asymetric syntheses, see: Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552 and references cited therein.
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44. For a highlight see: Bolm, C.; Bienewald, F.; Seger, A. Angew. Chem. Int. Ed. Engl. 1996, 35, 1657 and references cited therein.
45. The formation of cyclopropane by 1,3-elimination between an organogembismetallic and a methoxymethyl ether was already described: (a) Marek, I.; Beruben, D.; Normant, J. F. Tetrahedron Lett. 1995, 36, 3695. (b) Beruben, D.; Marek, I.; Normant, J. F.; Platzer, N. J. Org. Chem. 1995, 60, 2488. (c) Beruben, D.; Marek, I.; Normant, J. F.; Platzer, N. Tetrahedron Lett. 1993, 34, 7575.
46. The formation of cyclopropane by 1,3-elimination between an organogembismetallic and a methoxymethyl ether was already described: (a) Marek, I.; Beruben, D.; Normant, J. F. Tetrahedron Lett. 1995, 36, 3695. (b) Beruben, D.; Marek, I.; Normant, J. F.; Platzer, N. J. Org. Chem. 1995, 60, 2488. (c) Beruben, D.; Marek, I.; Normant, J. F.; Platzer, N. Tetrahedron Lett. 1993, 34, 7575.
47. The formation of cyclopropane by 1,3-elimination between an organogembismetallic and a methoxymethyl ether was already described: (a) Marek, I.; Beruben, D.; Normant, J. F. Tetrahedron Lett. 1995, 36, 3695. (b) Beruben, D.; Marek, I.; Normant, J. F.; Platzer, N. J. Org. Chem. 1995, 60, 2488. (c) Beruben, D.; Marek, I.; Normant, J. F.; Platzer, N. Tetrahedron Lett. 1993, 34, 7575.
48. For some representative formations of chiral cyclopropanes, see: (a) Charette, A. B.; Marcoux, J. F. Synlett 1995, 1197 and references cited therein. (b) Salaün, J. Chem. Rev. 1989, 89, 1247. (c) Romo, D.; Meyers, A. I. J. Org. Chem. 1992, 57, 6265. (d) Davies, H. M. L.; Huby, N. J. S.; Cantrell, W. R., Jr.; Olive, J. L. J. Am. Chem. Soc. 1993, 115, 9468. (e) Doyle, M. P. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; Chapter 3. (f) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (g) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (h) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584.
49. For some representative formations of chiral cyclopropanes, see: (a) Charette, A. B.; Marcoux, J. F. Synlett 1995, 1197 and references cited therein. (b) Salaün, J. Chem. Rev. 1989, 89, 1247. (c) Romo, D.; Meyers, A. I. J. Org. Chem. 1992, 57, 6265. (d) Davies, H. M. L.; Huby, N. J. S.; Cantrell, W. R., Jr.; Olive, J. L. J. Am. Chem. Soc. 1993, 115, 9468. (e) Doyle, M. P. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; Chapter 3. (f) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (g) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (h) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584.
50. For some representative formations of chiral cyclopropanes, see: (a) Charette, A. B.; Marcoux, J. F. Synlett 1995, 1197 and references cited therein. (b) Salaün, J. Chem. Rev. 1989, 89, 1247. (c) Romo, D.; Meyers, A. I. J. Org. Chem. 1992, 57, 6265. (d) Davies, H. M. L.; Huby, N. J. S.; Cantrell, W. R., Jr.; Olive, J. L. J. Am. Chem. Soc. 1993, 115, 9468. (e) Doyle, M. P. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; Chapter 3. (f) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (g) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (h) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584.
51. For some representative formations of chiral cyclopropanes, see: (a) Charette, A. B.; Marcoux, J. F. Synlett 1995, 1197 and references cited therein. (b) Salaün, J. Chem. Rev. 1989, 89, 1247. (c) Romo, D.; Meyers, A. I. J. Org. Chem. 1992, 57, 6265. (d) Davies, H. M. L.; Huby, N. J. S.; Cantrell, W. R., Jr.; Olive, J. L. J. Am. Chem. Soc. 1993, 115, 9468. (e) Doyle, M. P. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; Chapter 3. (f) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (g) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (h) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584.
52. For some representative formations of chiral cyclopropanes, see: (a) Charette, A. B.; Marcoux, J. F. Synlett 1995, 1197 and references cited therein. (b) Salaün, J. Chem. Rev. 1989, 89, 1247. (c) Romo, D.; Meyers, A. I. J. Org. Chem. 1992, 57, 6265. (d) Davies, H. M. L.; Huby, N. J. S.; Cantrell, W. R., Jr.; Olive, J. L. J. Am. Chem. Soc. 1993, 115, 9468. (e) Doyle, M. P. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; Chapter 3. (f) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (g) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (h) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584.
53. For some representative formations of chiral cyclopropanes, see: (a) Charette, A. B.; Marcoux, J. F. Synlett 1995, 1197 and references cited therein. (b) Salaün, J. Chem. Rev. 1989, 89, 1247. (c) Romo, D.; Meyers, A. I. J. Org. Chem. 1992, 57, 6265. (d) Davies, H. M. L.; Huby, N. J. S.; Cantrell, W. R., Jr.; Olive, J. L. J. Am. Chem. Soc. 1993, 115, 9468. (e) Doyle, M. P. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; Chapter 3. (f) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (g) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (h) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584.
54. For some representative formations of chiral cyclopropanes, see: (a) Charette, A. B.; Marcoux, J. F. Synlett 1995, 1197 and references cited therein. (b) Salaün, J. Chem. Rev. 1989, 89, 1247. (c) Romo, D.; Meyers, A. I. J. Org. Chem. 1992, 57, 6265. (d) Davies, H. M. L.; Huby, N. J. S.; Cantrell, W. R., Jr.; Olive, J. L. J. Am. Chem. Soc. 1993, 115, 9468. (e) Doyle, M. P. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; Chapter 3. (f) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (g) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (h) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584.
55. For some representative formations of chiral cyclopropanes, see: (a) Charette, A. B.; Marcoux, J. F. Synlett 1995, 1197 and references cited therein. (b) Salaün, J. Chem. Rev. 1989, 89, 1247. (c) Romo, D.; Meyers, A. I. J. Org. Chem. 1992, 57, 6265. (d) Davies, H. M. L.; Huby, N. J. S.; Cantrell, W. R., Jr.; Olive, J. L. J. Am. Chem. Soc. 1993, 115, 9468. (e) Doyle, M. P. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; Chapter 3. (f) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (g) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (h) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584.
56. Krief, A.; Hobe, M. Tetrahedron Lett. 1992, 33, 6529.
57. For a previous report on the synthesis of chiral cyclopropane mediated by a stoichiometric amount of (-)-sparteine see: Paetow, M.; Kotthaus, M.; Grehl, M.; Frölich, R.; Hoppe, D. Synlett 1994, 1034.
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