High-Diastereoselective and Enantioselective Cyclopropanation of α,β-Unsaturated Fischer Carbene Complexes: Synthesis of Chiral 1,2-Disubstituted and 1,2,3-Trisubstituted Cyclopropanes

Journal of Organic Chemistry

Volumn 62, Issue 20, 1997, Pages 6870-6875

  Barluenga, José ^a   Bernad Jr , Pablo L ^a   Concellón, José M ^a   Piñera Nicolás, Alejandro ^a   García Granda, Santiago ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; CYCLOPROPANE;

ARTICLE; CHIRALITY; CYCLIZATION; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030795135     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9708708     Document Type: Article

References (66)

1. For recent reviews of transition metal carbene complex chemistry, see: (a) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (b) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Chemistry; Verlag Chemie: Deerfield Beach, 1984. (c) Wulff, W. D. In Advances in Metal-Organic Chemistry, Liebeskind, L. S., Ed.; JAI: Greenwich, 1989; Vol. 5, p 209. (d) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1065. (e) Wulff, W. D. In Comprehensive Organic Synthesis II, Abel, A. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 469. (f) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, A. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 549.
2. For recent reviews of transition metal carbene complex chemistry, see: (a) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (b) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Chemistry; Verlag Chemie: Deerfield Beach, 1984. (c) Wulff, W. D. In Advances in Metal-Organic Chemistry, Liebeskind, L. S., Ed.; JAI: Greenwich, 1989; Vol. 5, p 209. (d) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1065. (e) Wulff, W. D. In Comprehensive Organic Synthesis II, Abel, A. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 469. (f) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, A. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 549.
3. For recent reviews of transition metal carbene complex chemistry, see: (a) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (b) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Chemistry; Verlag Chemie: Deerfield Beach, 1984. (c) Wulff, W. D. In Advances in Metal-Organic Chemistry, Liebeskind, L. S., Ed.; JAI: Greenwich, 1989; Vol. 5, p 209. (d) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1065. (e) Wulff, W. D. In Comprehensive Organic Synthesis II, Abel, A. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 469. (f) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, A. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 549.
4. For recent reviews of transition metal carbene complex chemistry, see: (a) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (b) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Chemistry; Verlag Chemie: Deerfield Beach, 1984. (c) Wulff, W. D. In Advances in Metal-Organic Chemistry, Liebeskind, L. S., Ed.; JAI: Greenwich, 1989; Vol. 5, p 209. (d) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1065. (e) Wulff, W. D. In Comprehensive Organic Synthesis II, Abel, A. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 469. (f) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, A. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 549.
5. For recent reviews of transition metal carbene complex chemistry, see: (a) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (b) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Chemistry; Verlag Chemie: Deerfield Beach, 1984. (c) Wulff, W. D. In Advances in Metal-Organic Chemistry, Liebeskind, L. S., Ed.; JAI: Greenwich, 1989; Vol. 5, p 209. (d) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1065. (e) Wulff, W. D. In Comprehensive Organic Synthesis II, Abel, A. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 469. (f) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, A. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 549.
6. For recent reviews of transition metal carbene complex chemistry, see: (a) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (b) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Chemistry; Verlag Chemie: Deerfield Beach, 1984. (c) Wulff, W. D. In Advances in Metal-Organic Chemistry, Liebeskind, L. S., Ed.; JAI: Greenwich, 1989; Vol. 5, p 209. (d) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1065. (e) Wulff, W. D. In Comprehensive Organic Synthesis II, Abel, A. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 469. (f) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, A. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 549.
7. Cycloaddition with alkynes: (a) Herndon, J. W.; Turner, S. U.; Schnatter, W. F. K. J. Am. Chem. Soc. 1988, 110, 3334. (b) Herndon, J. W.; Turner, S. U. Tetrahedron Lett. 1989, 30, 295. (c) Herndon, J. W.; Turner, S. U.; McMullen, L. A.; Matasi, J. J.; Schnatter, W. F. K.; Daitch, C. E. Comments Inorg. Chem. 1990, 10, 1. (d) Turner, S. U.; Herndon, J. W.; McMullen, J. A. J. Am. Chem. Soc. 1992, 114, 8394. Intramolecular reaction from 2-alkenylcyclopropylcarbene complexes; (e) Herndon, J. W.; McMullen, L. A. J. Am. Chem. Soc. 1989, 111, 6854. (f) Herndon, J. W.; Hill, D. K.; McMullen, L. A. Tetrahedron Lett. 1995, 36, 5687. (g) Hill, D. K.; Herndon, J. W. Tetrahedron Lett. 1996, 37, 1359.
8. Cycloaddition with alkynes: (a) Herndon, J. W.; Turner, S. U.; Schnatter, W. F. K. J. Am. Chem. Soc. 1988, 110, 3334. (b) Herndon, J. W.; Turner, S. U. Tetrahedron Lett. 1989, 30, 295. (c) Herndon, J. W.; Turner, S. U.; McMullen, L. A.; Matasi, J. J.; Schnatter, W. F. K.; Daitch, C. E. Comments Inorg. Chem. 1990, 10, 1. (d) Turner, S. U.; Herndon, J. W.; McMullen, J. A. J. Am. Chem. Soc. 1992, 114, 8394. Intramolecular reaction from 2-alkenylcyclopropylcarbene complexes; (e) Herndon, J. W.; McMullen, L. A. J. Am. Chem. Soc. 1989, 111, 6854. (f) Herndon, J. W.; Hill, D. K.; McMullen, L. A. Tetrahedron Lett. 1995, 36, 5687. (g) Hill, D. K.; Herndon, J. W. Tetrahedron Lett. 1996, 37, 1359.
9. Cycloaddition with alkynes: (a) Herndon, J. W.; Turner, S. U.; Schnatter, W. F. K. J. Am. Chem. Soc. 1988, 110, 3334. (b) Herndon, J. W.; Turner, S. U. Tetrahedron Lett. 1989, 30, 295. (c) Herndon, J. W.; Turner, S. U.; McMullen, L. A.; Matasi, J. J.; Schnatter, W. F. K.; Daitch, C. E. Comments Inorg. Chem. 1990, 10, 1. (d) Turner, S. U.; Herndon, J. W.; McMullen, J. A. J. Am. Chem. Soc. 1992, 114, 8394. Intramolecular reaction from 2-alkenylcyclopropylcarbene complexes; (e) Herndon, J. W.; McMullen, L. A. J. Am. Chem. Soc. 1989, 111, 6854. (f) Herndon, J. W.; Hill, D. K.; McMullen, L. A. Tetrahedron Lett. 1995, 36, 5687. (g) Hill, D. K.; Herndon, J. W. Tetrahedron Lett. 1996, 37, 1359.
10. Cycloaddition with alkynes: (a) Herndon, J. W.; Turner, S. U.; Schnatter, W. F. K. J. Am. Chem. Soc. 1988, 110, 3334. (b) Herndon, J. W.; Turner, S. U. Tetrahedron Lett. 1989, 30, 295. (c) Herndon, J. W.; Turner, S. U.; McMullen, L. A.; Matasi, J. J.; Schnatter, W. F. K.; Daitch, C. E. Comments Inorg. Chem. 1990, 10, 1. (d) Turner, S. U.; Herndon, J. W.; McMullen, J. A. J. Am. Chem. Soc. 1992, 114, 8394. Intramolecular reaction from 2-alkenylcyclopropylcarbene complexes; (e) Herndon, J. W.; McMullen, L. A. J. Am. Chem. Soc. 1989, 111, 6854. (f) Herndon, J. W.; Hill, D. K.; McMullen, L. A. Tetrahedron Lett. 1995, 36, 5687. (g) Hill, D. K.; Herndon, J. W. Tetrahedron Lett. 1996, 37, 1359.
11. Cycloaddition with alkynes: (a) Herndon, J. W.; Turner, S. U.; Schnatter, W. F. K. J. Am. Chem. Soc. 1988, 110, 3334. (b) Herndon, J. W.; Turner, S. U. Tetrahedron Lett. 1989, 30, 295. (c) Herndon, J. W.; Turner, S. U.; McMullen, L. A.; Matasi, J. J.; Schnatter, W. F. K.; Daitch, C. E. Comments Inorg. Chem. 1990, 10, 1. (d) Turner, S. U.; Herndon, J. W.; McMullen, J. A. J. Am. Chem. Soc. 1992, 114, 8394. Intramolecular reaction from 2-alkenylcyclopropylcarbene complexes; (e) Herndon, J. W.; McMullen, L. A. J. Am. Chem. Soc. 1989, 111, 6854. (f) Herndon, J. W.; Hill, D. K.; McMullen, L. A. Tetrahedron Lett. 1995, 36, 5687. (g) Hill, D. K.; Herndon, J. W. Tetrahedron Lett. 1996, 37, 1359.
12. Cycloaddition with alkynes: (a) Herndon, J. W.; Turner, S. U.; Schnatter, W. F. K. J. Am. Chem. Soc. 1988, 110, 3334. (b) Herndon, J. W.; Turner, S. U. Tetrahedron Lett. 1989, 30, 295. (c) Herndon, J. W.; Turner, S. U.; McMullen, L. A.; Matasi, J. J.; Schnatter, W. F. K.; Daitch, C. E. Comments Inorg. Chem. 1990, 10, 1. (d) Turner, S. U.; Herndon, J. W.; McMullen, J. A. J. Am. Chem. Soc. 1992, 114, 8394. Intramolecular reaction from 2-alkenylcyclopropylcarbene complexes; (e) Herndon, J. W.; McMullen, L. A. J. Am. Chem. Soc. 1989, 111, 6854. (f) Herndon, J. W.; Hill, D. K.; McMullen, L. A. Tetrahedron Lett. 1995, 36, 5687. (g) Hill, D. K.; Herndon, J. W. Tetrahedron Lett. 1996, 37, 1359.
13. Cycloaddition with alkynes: (a) Herndon, J. W.; Turner, S. U.; Schnatter, W. F. K. J. Am. Chem. Soc. 1988, 110, 3334. (b) Herndon, J. W.; Turner, S. U. Tetrahedron Lett. 1989, 30, 295. (c) Herndon, J. W.; Turner, S. U.; McMullen, L. A.; Matasi, J. J.; Schnatter, W. F. K.; Daitch, C. E. Comments Inorg. Chem. 1990, 10, 1. (d) Turner, S. U.; Herndon, J. W.; McMullen, J. A. J. Am. Chem. Soc. 1992, 114, 8394. Intramolecular reaction from 2-alkenylcyclopropylcarbene complexes; (e) Herndon, J. W.; McMullen, L. A. J. Am. Chem. Soc. 1989, 111, 6854. (f) Herndon, J. W.; Hill, D. K.; McMullen, L. A. Tetrahedron Lett. 1995, 36, 5687. (g) Hill, D. K.; Herndon, J. W. Tetrahedron Lett. 1996, 37, 1359.
14. Herndon, J. W.; Patel, P. P. Tetrahedron Lett. 1997, 38, 59.
15. Herndon, J. W.; Matasi, J. J. J. Org. Chem. 1990, 55, 786.
16. Starting from tungsten carbene complexes: (a) Herndon, J. W.; Chatterjee, G.; Patel, P. P.; Matasi, J. J.; Turner, S. U.; Harp, J. J.; Reid, M. D. J. Am. Chem. Soc. 1991, 113, 7808. (b) Herndon, J. W.; Zora, M.; Patel, P. P.; Chatterjee, G.; Matasi, J. J.; Turner, S. U. Tetrahedron 1993, 49, 5507. From molybdenum carbene complexes: (c) Herndon, J. W.; Zora, M. Synlett 1993, 363.
17. Starting from tungsten carbene complexes: (a) Herndon, J. W.; Chatterjee, G.; Patel, P. P.; Matasi, J. J.; Turner, S. U.; Harp, J. J.; Reid, M. D. J. Am. Chem. Soc. 1991, 113, 7808. (b) Herndon, J. W.; Zora, M.; Patel, P. P.; Chatterjee, G.; Matasi, J. J.; Turner, S. U. Tetrahedron 1993, 49, 5507. From molybdenum carbene complexes: (c) Herndon, J. W.; Zora, M. Synlett 1993, 363.
18. Starting from tungsten carbene complexes: (a) Herndon, J. W.; Chatterjee, G.; Patel, P. P.; Matasi, J. J.; Turner, S. U.; Harp, J. J.; Reid, M. D. J. Am. Chem. Soc. 1991, 113, 7808. (b) Herndon, J. W.; Zora, M.; Patel, P. P.; Chatterjee, G.; Matasi, J. J.; Turner, S. U. Tetrahedron 1993, 49, 5507. From molybdenum carbene complexes: (c) Herndon, J. W.; Zora, M. Synlett 1993, 363.
19. Herndon, J. W.; Reid, M. D. J. Am. Chem. Soc. 1994, 116, 383.
20. Herndon, J. W.; Turner, S. U. J. Org. Chem. 1991, 56, 286.
21. (a) Herndon, J. W. Organometallics 1994, 13, 3370.
22. (b) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699.
23. (c) Herndon, J. W.; Hayford, A. Organometallics 1995, 14, 1556.
24. (d) Herndon, J. W.; Patel, P. P. J. Org. Chem. 1996, 61, 4500.
25. (e) Krestschik, O.; Herndon, J. W.; Patel, P. P. Organometallics 1996, 15, 3625.
26. (a) Hegedus, L. S.; de Weck, G.; D'Andrea, S. J. Am. Chem. Soc. 1988, 110, 2122.
27. (b) Hegedus, L. S.; Bates, R. W.; Söderberg, B. C. J. Am. Chem. Soc. 1991, 113, 923.
28. (c) Schwindt, M. A.; Miller, J. R.; Hegedus, L. S. J. Organomet. Chem. 1991, 413, 143.
29. Preparation of esters: (a) Casey, C. P.; Burkhardt, T. J.; Bunell, C. A.; Calabrese, J. C. J. Am. Chem. Soc. 1977, 99, 2127. (b) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. (c) Erker, G.; Sosna, F. Organometallics 1990, 9, 1949. (d) Lluch, A.; Jordi, L.; Sanchez-Baeza, F.; Ricart, S.; Camps, F.; Moretó, J. M. Tetrahedron Lett. 1992, 33, 3021. Synthesis of aldehydes: (e) Fischer, E. O.; Walz, S.; Kreis, G.; Kreissl, F. R. Chem. Ber. 1977, 770, 1651. (f) Casey, C. P.; Neumann, S. M. J. Am. Chem. Soc. 1977, 99, 1651. Synthesis of methyl vinyl ethers: (g) Fischer, E. O.; Plabst, D. Chem. Ber. 1974, 707, 3326. Obtention of enol ethers: (h) Casey, C. P.; Bertz, S. H.; Burkhardt, T. J. Tetrahedron Lett, 1973, 1421. (i) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. Preparation of methyl ketones: (j) Barluenga, J.; Bernad, P. L., Jr.; Concellón, J. M. Tetrahedron Lett. 1994, 35, 9471.
30. Preparation of esters: (a) Casey, C. P.; Burkhardt, T. J.; Bunell, C. A.; Calabrese, J. C. J. Am. Chem. Soc. 1977, 99, 2127. (b) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. (c) Erker, G.; Sosna, F. Organometallics 1990, 9, 1949. (d) Lluch, A.; Jordi, L.; Sanchez-Baeza, F.; Ricart, S.; Camps, F.; Moretó, J. M. Tetrahedron Lett. 1992, 33, 3021. Synthesis of aldehydes: (e) Fischer, E. O.; Walz, S.; Kreis, G.; Kreissl, F. R. Chem. Ber. 1977, 770, 1651. (f) Casey, C. P.; Neumann, S. M. J. Am. Chem. Soc. 1977, 99, 1651. Synthesis of methyl vinyl ethers: (g) Fischer, E. O.; Plabst, D. Chem. Ber. 1974, 707, 3326. Obtention of enol ethers: (h) Casey, C. P.; Bertz, S. H.; Burkhardt, T. J. Tetrahedron Lett, 1973, 1421. (i) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. Preparation of methyl ketones: (j) Barluenga, J.; Bernad, P. L., Jr.; Concellón, J. M. Tetrahedron Lett. 1994, 35, 9471.
31. Preparation of esters: (a) Casey, C. P.; Burkhardt, T. J.; Bunell, C. A.; Calabrese, J. C. J. Am. Chem. Soc. 1977, 99, 2127. (b) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. (c) Erker, G.; Sosna, F. Organometallics 1990, 9, 1949. (d) Lluch, A.; Jordi, L.; Sanchez-Baeza, F.; Ricart, S.; Camps, F.; Moretó, J. M. Tetrahedron Lett. 1992, 33, 3021. Synthesis of aldehydes: (e) Fischer, E. O.; Walz, S.; Kreis, G.; Kreissl, F. R. Chem. Ber. 1977, 770, 1651. (f) Casey, C. P.; Neumann, S. M. J. Am. Chem. Soc. 1977, 99, 1651. Synthesis of methyl vinyl ethers: (g) Fischer, E. O.; Plabst, D. Chem. Ber. 1974, 707, 3326. Obtention of enol ethers: (h) Casey, C. P.; Bertz, S. H.; Burkhardt, T. J. Tetrahedron Lett, 1973, 1421. (i) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. Preparation of methyl ketones: (j) Barluenga, J.; Bernad, P. L., Jr.; Concellón, J. M. Tetrahedron Lett. 1994, 35, 9471.
32. Preparation of esters: (a) Casey, C. P.; Burkhardt, T. J.; Bunell, C. A.; Calabrese, J. C. J. Am. Chem. Soc. 1977, 99, 2127. (b) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. (c) Erker, G.; Sosna, F. Organometallics 1990, 9, 1949. (d) Lluch, A.; Jordi, L.; Sanchez-Baeza, F.; Ricart, S.; Camps, F.; Moretó, J. M. Tetrahedron Lett. 1992, 33, 3021. Synthesis of aldehydes: (e) Fischer, E. O.; Walz, S.; Kreis, G.; Kreissl, F. R. Chem. Ber. 1977, 770, 1651. (f) Casey, C. P.; Neumann, S. M. J. Am. Chem. Soc. 1977, 99, 1651. Synthesis of methyl vinyl ethers: (g) Fischer, E. O.; Plabst, D. Chem. Ber. 1974, 707, 3326. Obtention of enol ethers: (h) Casey, C. P.; Bertz, S. H.; Burkhardt, T. J. Tetrahedron Lett, 1973, 1421. (i) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. Preparation of methyl ketones: (j) Barluenga, J.; Bernad, P. L., Jr.; Concellón, J. M. Tetrahedron Lett. 1994, 35, 9471.
33. Preparation of esters: (a) Casey, C. P.; Burkhardt, T. J.; Bunell, C. A.; Calabrese, J. C. J. Am. Chem. Soc. 1977, 99, 2127. (b) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. (c) Erker, G.; Sosna, F. Organometallics 1990, 9, 1949. (d) Lluch, A.; Jordi, L.; Sanchez-Baeza, F.; Ricart, S.; Camps, F.; Moretó, J. M. Tetrahedron Lett. 1992, 33, 3021. Synthesis of aldehydes: (e) Fischer, E. O.; Walz, S.; Kreis, G.; Kreissl, F. R. Chem. Ber. 1977, 770, 1651. (f) Casey, C. P.; Neumann, S. M. J. Am. Chem. Soc. 1977, 99, 1651. Synthesis of methyl vinyl ethers: (g) Fischer, E. O.; Plabst, D. Chem. Ber. 1974, 707, 3326. Obtention of enol ethers: (h) Casey, C. P.; Bertz, S. H.; Burkhardt, T. J. Tetrahedron Lett, 1973, 1421. (i) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. Preparation of methyl ketones: (j) Barluenga, J.; Bernad, P. L., Jr.; Concellón, J. M. Tetrahedron Lett. 1994, 35, 9471.
34. Preparation of esters: (a) Casey, C. P.; Burkhardt, T. J.; Bunell, C. A.; Calabrese, J. C. J. Am. Chem. Soc. 1977, 99, 2127. (b) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. (c) Erker, G.; Sosna, F. Organometallics 1990, 9, 1949. (d) Lluch, A.; Jordi, L.; Sanchez-Baeza, F.; Ricart, S.; Camps, F.; Moretó, J. M. Tetrahedron Lett. 1992, 33, 3021. Synthesis of aldehydes: (e) Fischer, E. O.; Walz, S.; Kreis, G.; Kreissl, F. R. Chem. Ber. 1977, 770, 1651. (f) Casey, C. P.; Neumann, S. M. J. Am. Chem. Soc. 1977, 99, 1651. Synthesis of methyl vinyl ethers: (g) Fischer, E. O.; Plabst, D. Chem. Ber. 1974, 707, 3326. Obtention of enol ethers: (h) Casey, C. P.; Bertz, S. H.; Burkhardt, T. J. Tetrahedron Lett, 1973, 1421. (i) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. Preparation of methyl ketones: (j) Barluenga, J.; Bernad, P. L., Jr.; Concellón, J. M. Tetrahedron Lett. 1994, 35, 9471.
35. Preparation of esters: (a) Casey, C. P.; Burkhardt, T. J.; Bunell, C. A.; Calabrese, J. C. J. Am. Chem. Soc. 1977, 99, 2127. (b) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. (c) Erker, G.; Sosna, F. Organometallics 1990, 9, 1949. (d) Lluch, A.; Jordi, L.; Sanchez-Baeza, F.; Ricart, S.; Camps, F.; Moretó, J. M. Tetrahedron Lett. 1992, 33, 3021. Synthesis of aldehydes: (e) Fischer, E. O.; Walz, S.; Kreis, G.; Kreissl, F. R. Chem. Ber. 1977, 770, 1651. (f) Casey, C. P.; Neumann, S. M. J. Am. Chem. Soc. 1977, 99, 1651. Synthesis of methyl vinyl ethers: (g) Fischer, E. O.; Plabst, D. Chem. Ber. 1974, 707, 3326. Obtention of enol ethers: (h) Casey, C. P.; Bertz, S. H.; Burkhardt, T. J. Tetrahedron Lett, 1973, 1421. (i) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. Preparation of methyl ketones: (j) Barluenga, J.; Bernad, P. L., Jr.; Concellón, J. M. Tetrahedron Lett. 1994, 35, 9471.
36. Preparation of esters: (a) Casey, C. P.; Burkhardt, T. J.; Bunell, C. A.; Calabrese, J. C. J. Am. Chem. Soc. 1977, 99, 2127. (b) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. (c) Erker, G.; Sosna, F. Organometallics 1990, 9, 1949. (d) Lluch, A.; Jordi, L.; Sanchez-Baeza, F.; Ricart, S.; Camps, F.; Moretó, J. M. Tetrahedron Lett. 1992, 33, 3021. Synthesis of aldehydes: (e) Fischer, E. O.; Walz, S.; Kreis, G.; Kreissl, F. R. Chem. Ber. 1977, 770, 1651. (f) Casey, C. P.; Neumann, S. M. J. Am. Chem. Soc. 1977, 99, 1651. Synthesis of methyl vinyl ethers: (g) Fischer, E. O.; Plabst, D. Chem. Ber. 1974, 707, 3326. Obtention of enol ethers: (h) Casey, C. P.; Bertz, S. H.; Burkhardt, T. J. Tetrahedron Lett, 1973, 1421. (i) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. Preparation of methyl ketones: (j) Barluenga, J.; Bernad, P. L., Jr.; Concellón, J. M. Tetrahedron Lett. 1994, 35, 9471.
37. Preparation of esters: (a) Casey, C. P.; Burkhardt, T. J.; Bunell, C. A.; Calabrese, J. C. J. Am. Chem. Soc. 1977, 99, 2127. (b) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. (c) Erker, G.; Sosna, F. Organometallics 1990, 9, 1949. (d) Lluch, A.; Jordi, L.; Sanchez-Baeza, F.; Ricart, S.; Camps, F.; Moretó, J. M. Tetrahedron Lett. 1992, 33, 3021. Synthesis of aldehydes: (e) Fischer, E. O.; Walz, S.; Kreis, G.; Kreissl, F. R. Chem. Ber. 1977, 770, 1651. (f) Casey, C. P.; Neumann, S. M. J. Am. Chem. Soc. 1977, 99, 1651. Synthesis of methyl vinyl ethers: (g) Fischer, E. O.; Plabst, D. Chem. Ber. 1974, 707, 3326. Obtention of enol ethers: (h) Casey, C. P.; Bertz, S. H.; Burkhardt, T. J. Tetrahedron Lett, 1973, 1421. (i) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. Preparation of methyl ketones: (j) Barluenga, J.; Bernad, P. L., Jr.; Concellón, J. M. Tetrahedron Lett. 1994, 35, 9471.
38. Preparation of esters: (a) Casey, C. P.; Burkhardt, T. J.; Bunell, C. A.; Calabrese, J. C. J. Am. Chem. Soc. 1977, 99, 2127. (b) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. (c) Erker, G.; Sosna, F. Organometallics 1990, 9, 1949. (d) Lluch, A.; Jordi, L.; Sanchez-Baeza, F.; Ricart, S.; Camps, F.; Moretó, J. M. Tetrahedron Lett. 1992, 33, 3021. Synthesis of aldehydes: (e) Fischer, E. O.; Walz, S.; Kreis, G.; Kreissl, F. R. Chem. Ber. 1977, 770, 1651. (f) Casey, C. P.; Neumann, S. M. J. Am. Chem. Soc. 1977, 99, 1651. Synthesis of methyl vinyl ethers: (g) Fischer, E. O.; Plabst, D. Chem. Ber. 1974, 707, 3326. Obtention of enol ethers: (h) Casey, C. P.; Bertz, S. H.; Burkhardt, T. J. Tetrahedron Lett, 1973, 1421. (i) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543. Preparation of methyl ketones: (j) Barluenga, J.; Bernad, P. L., Jr.; Concellón, J. M. Tetrahedron Lett. 1994, 35, 9471.
39. Reissig, H. U. Organic synthesis via cyclopropanes: principles and applications. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: New York, 1987; Chapter 8.
40. Liu, H. W.; Walsh, C. T. Biochemistry of the cyclopropyl group. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: New York, 1987; Chapter 16.
41. Suckling, C. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 537.
42. For the use of chiral auxiliaries in asymmetric Simmons - Smith reactions: (a) Charette, A. B.; Marcoux, J. F. Synlett 1995, 1997. (b) Charette, A. B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651 and references cited therein. For the asymmetric cyclopropanation by diazoalkanes: (c) Doyle, M. P. Asymmetric cyclopropanation. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 3. (d) Corey, E. J.; Grant, T. G. Tetrahedron Lett. 1994, 35, 5373. (e) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 37, 430.
43. For the use of chiral auxiliaries in asymmetric Simmons - Smith reactions: (a) Charette, A. B.; Marcoux, J. F. Synlett 1995, 1997. (b) Charette, A. B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651 and references cited therein. For the asymmetric cyclopropanation by diazoalkanes: (c) Doyle, M. P. Asymmetric cyclopropanation. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 3. (d) Corey, E. J.; Grant, T. G. Tetrahedron Lett. 1994, 35, 5373. (e) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 37, 430.
44. For the use of chiral auxiliaries in asymmetric Simmons - Smith reactions: (a) Charette, A. B.; Marcoux, J. F. Synlett 1995, 1997. (b) Charette, A. B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651 and references cited therein. For the asymmetric cyclopropanation by diazoalkanes: (c) Doyle, M. P. Asymmetric cyclopropanation. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 3. (d) Corey, E. J.; Grant, T. G. Tetrahedron Lett. 1994, 35, 5373. (e) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 37, 430.
45. For the use of chiral auxiliaries in asymmetric Simmons - Smith reactions: (a) Charette, A. B.; Marcoux, J. F. Synlett 1995, 1997. (b) Charette, A. B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651 and references cited therein. For the asymmetric cyclopropanation by diazoalkanes: (c) Doyle, M. P. Asymmetric cyclopropanation. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 3. (d) Corey, E. J.; Grant, T. G. Tetrahedron Lett. 1994, 35, 5373. (e) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 37, 430.
46. For the use of chiral auxiliaries in asymmetric Simmons - Smith reactions: (a) Charette, A. B.; Marcoux, J. F. Synlett 1995, 1997. (b) Charette, A. B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651 and references cited therein. For the asymmetric cyclopropanation by diazoalkanes: (c) Doyle, M. P. Asymmetric cyclopropanation. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 3. (d) Corey, E. J.; Grant, T. G. Tetrahedron Lett. 1994, 35, 5373. (e) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 37, 430.
47. Synthesis of 1,2,3-trisubstituted cydopropanes; (a) Ito, K.; Katsuki, T. Synlett 1993, 638. (b) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (c) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (d) Kunz, T.; Reissig, H. U. Tetrahedron Lett. 1989, 30, 2079. (e) Dammast, F.; Reissig, H. U. Chem. Ber. 1993, 126, 2449. (f) Dammast, F.; Reissig, H. U. Chem. Ber. 1993, 126, 2727.
48. Synthesis of 1,2,3-trisubstituted cydopropanes; (a) Ito, K.; Katsuki, T. Synlett 1993, 638. (b) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (c) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (d) Kunz, T.; Reissig, H. U. Tetrahedron Lett. 1989, 30, 2079. (e) Dammast, F.; Reissig, H. U. Chem. Ber. 1993, 126, 2449. (f) Dammast, F.; Reissig, H. U. Chem. Ber. 1993, 126, 2727.
49. Synthesis of 1,2,3-trisubstituted cydopropanes; (a) Ito, K.; Katsuki, T. Synlett 1993, 638. (b) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (c) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (d) Kunz, T.; Reissig, H. U. Tetrahedron Lett. 1989, 30, 2079. (e) Dammast, F.; Reissig, H. U. Chem. Ber. 1993, 126, 2449. (f) Dammast, F.; Reissig, H. U. Chem. Ber. 1993, 126, 2727.
50. Synthesis of 1,2,3-trisubstituted cydopropanes; (a) Ito, K.; Katsuki, T. Synlett 1993, 638. (b) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (c) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (d) Kunz, T.; Reissig, H. U. Tetrahedron Lett. 1989, 30, 2079. (e) Dammast, F.; Reissig, H. U. Chem. Ber. 1993, 126, 2449. (f) Dammast, F.; Reissig, H. U. Chem. Ber. 1993, 126, 2727.
51. Synthesis of 1,2,3-trisubstituted cydopropanes; (a) Ito, K.; Katsuki, T. Synlett 1993, 638. (b) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (c) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (d) Kunz, T.; Reissig, H. U. Tetrahedron Lett. 1989, 30, 2079. (e) Dammast, F.; Reissig, H. U. Chem. Ber. 1993, 126, 2449. (f) Dammast, F.; Reissig, H. U. Chem. Ber. 1993, 126, 2727.
52. Synthesis of 1,2,3-trisubstituted cydopropanes; (a) Ito, K.; Katsuki, T. Synlett 1993, 638. (b) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (c) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (d) Kunz, T.; Reissig, H. U. Tetrahedron Lett. 1989, 30, 2079. (e) Dammast, F.; Reissig, H. U. Chem. Ber. 1993, 126, 2449. (f) Dammast, F.; Reissig, H. U. Chem. Ber. 1993, 126, 2727.
53. Barluenga, J.; Bernad, P. L., Jr.; Concellón, J. M. Tetrahedron Lett. 1995, 36, 3937.
54. Barluenga, J.; Montserrat, J. M.; Flórez, J.; García-Granda, S.; Martin, E. Angew. Chem., Int. Ed. Engt. 1994, 33, 1392.
55. Unpublished results. Different Fischer carbene complexes can be transformed into bromomethyl ketones by treatment with dibromomethyllithium.
56. Morris, D. G. Nuclear magnetic resonance and infrared spectra of cyclopropanes and cyclopropenes. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: New York, 1987; Chapter 3.
57. The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.
58. Evidence for ,π,π-attractive interactions: (a) Corey, E. J.; Matsumura, Y. Tetrahedron Lett, 1991, 32, 6289. (b) Corey, E. J.; Loh, T. P. J. Am. Chem. Soc. 1991, 113, 8966. (c) Hawking, J. M.; Loren, S. J. Am. Chem. Soc. 1991, 113, 7794 and references cited therein.
59. Evidence for ,π,π-attractive interactions: (a) Corey, E. J.; Matsumura, Y. Tetrahedron Lett, 1991, 32, 6289. (b) Corey, E. J.; Loh, T. P. J. Am. Chem. Soc. 1991, 113, 8966. (c) Hawking, J. M.; Loren, S. J. Am. Chem. Soc. 1991, 113, 7794 and references cited therein.
60. Evidence for ,π,π-attractive interactions: (a) Corey, E. J.; Matsumura, Y. Tetrahedron Lett, 1991, 32, 6289. (b) Corey, E. J.; Loh, T. P. J. Am. Chem. Soc. 1991, 113, 8966. (c) Hawking, J. M.; Loren, S. J. Am. Chem. Soc. 1991, 113, 7794 and references cited therein.
61. (a) Oppolzer, W.; Löher, H. J. Helv. Chim. Acta 1981, 64, 2808.
62. (b) d'Angelo, J.; Maddaluno, J. J. Am. Chem. Soc. 1986, 108, 8112.
63. Nakamura, E.; Tanaka, K.; Fujimura, T.; Aoki, S.; Williard, P. G. J. Am. Chem. Soc. 1993, 775, 9015.
64. Arndt, F. In Organic Syntheses; Blatt, A. H., Ed.; John Wiley and Sons: New York, 1948; Collect. Vol. 2, p 165.
65. (a) Barluenga, J.; Montserrat, J. M.; Flórez, J.; Garcia-Granda, S.; Martín, E. Chem. Eur. J. 1995, 1, 236.
66. (b) Aumann, R.; Heinen, H. Chem. Ber. 1987, 120, 537.