Dianion approach to chiral cyclopropene carboxylic acids

Organic Letters

Volumn 6, Issue 26, 2004, Pages 4937-4939

  Liao, Lian An ^a   Yan, Ni ^a   Fox, Joseph M ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; CARBOXYLIC ACID DERIVATIVE; FUNCTIONAL GROUP; PROPYLENE;

ARTICLE; CHIRALITY; ENANTIOSELECTIVITY; ORGANIC CHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

ANIONS; CARBOXYLIC ACIDS; CYCLOPROPANES; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 12344277594     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047837+     Document Type: Article

References (55)

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2. (b) Diaz-Requejo, M. M.; Mairena, M. A.; Belderrain, T. R.; Nicasio, M. C.; Trofimenko, S.; Perez, P. J. Chem. Communn. 2001, 1804 and references therein.
3. Reviews of cyclopropene formation and reactivity: (a) Halton, B.; Banwell, M. G. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1987; p 1224. (b) Baird, M. S. Top. Curr. Chem. 1988, 144, 137. (c) Baird, M. S.; Schmidt, T. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17a, p 114. (d) Baird, M. S.; Bushby, R. J.; Schmidt, T. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17d, p 2695. (e) Hopf, H. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17d, p 2745. (f) Padwa, A.; Fryxell, G. E. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; Jai Press: Greenwich, CT, 1991; Vol. 1.
4. Reviews of cyclopropene formation and reactivity: (a) Halton, B.; Banwell, M. G. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1987; p 1224. (b) Baird, M. S. Top. Curr. Chem. 1988, 144, 137. (c) Baird, M. S.; Schmidt, T. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17a, p 114. (d) Baird, M. S.; Bushby, R. J.; Schmidt, T. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17d, p 2695. (e) Hopf, H. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17d, p 2745. (f) Padwa, A.; Fryxell, G. E. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; Jai Press: Greenwich, CT, 1991; Vol. 1.
5. Reviews of cyclopropene formation and reactivity: (a) Halton, B.; Banwell, M. G. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1987; p 1224. (b) Baird, M. S. Top. Curr. Chem. 1988, 144, 137. (c) Baird, M. S.; Schmidt, T. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17a, p 114. (d) Baird, M. S.; Bushby, R. J.; Schmidt, T. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17d, p 2695. (e) Hopf, H. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17d, p 2745. (f) Padwa, A.; Fryxell, G. E. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; Jai Press: Greenwich, CT, 1991; Vol. 1.
6. Reviews of cyclopropene formation and reactivity: (a) Halton, B.; Banwell, M. G. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1987; p 1224. (b) Baird, M. S. Top. Curr. Chem. 1988, 144, 137. (c) Baird, M. S.; Schmidt, T. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17a, p 114. (d) Baird, M. S.; Bushby, R. J.; Schmidt, T. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17d, p 2695. (e) Hopf, H. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17d, p 2745. (f) Padwa, A.; Fryxell, G. E. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; Jai Press: Greenwich, CT, 1991; Vol. 1.
7. Reviews of cyclopropene formation and reactivity: (a) Halton, B.; Banwell, M. G. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1987; p 1224. (b) Baird, M. S. Top. Curr. Chem. 1988, 144, 137. (c) Baird, M. S.; Schmidt, T. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17a, p 114. (d) Baird, M. S.; Bushby, R. J.; Schmidt, T. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17d, p 2695. (e) Hopf, H. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17d, p 2745. (f) Padwa, A.; Fryxell, G. E. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; Jai Press: Greenwich, CT, 1991; Vol. 1.
8. Reviews of cyclopropene formation and reactivity: (a) Halton, B.; Banwell, M. G. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1987; p 1224. (b) Baird, M. S. Top. Curr. Chem. 1988, 144, 137. (c) Baird, M. S.; Schmidt, T. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17a, p 114. (d) Baird, M. S.; Bushby, R. J.; Schmidt, T. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17d, p 2695. (e) Hopf, H. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17d, p 2745. (f) Padwa, A.; Fryxell, G. E. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; Jai Press: Greenwich, CT, 1991; Vol. 1.
9. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
10. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
11. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
12. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
13. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
14. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
15. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
16. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
17. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
18. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
19. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
20. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
21. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
22. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
23. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
24. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
25. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
26. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
27. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
28. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
29. Recent, synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688. (e) Zohar, E.; Marek, I. Org. Lett 2004, 6, 341. Carbometalation reactions: (f) Fox, J. M.; Liao, L.-a. J. Am. Chem. Soc. 2002, 124, 14322. (g) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033 and references therein. Cyclizations and rearrangements: (h) Padwa, A.; Kassir, J. M.; Xu, S. L. J. Org. Chem. 1997, 62, 1642. (i) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164. (j) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc 2003, 125, 12386. (k) Al-Dulayymi, J.; Baird, M. S. Tetrahedron 1990, 46, 5703. Cycloadditions: (l) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron. Lett. 2000, 41, 4205. (m) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849. (n) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467. (o) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett 2001, 3, 3193. (p) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431. (q) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406. (r) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570. Ring-opening reactions: (s) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954. (t) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297. (u) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
30. Reactions of cyclopropenone ketals: Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295.
31. For a comprehensive bibliography of nonracemic cyclopropene synthesis, see ref 7a.
32. (a) Doyle, M. P.; Protopopova, M.; Müller, P.; Ene, D.; Shapiro, E. A. J. Am. Chem. Soc. 1994, 116, 8492,
33. (b) Müller, P.; Imogai, H. Tetrahedron: Asymmetry 1998, 9, 4419.
34. (c) Doyle, M. P.; Ene, D. G.; Forbes, D. C.; Pillow, T. H. Chem. Commun. 1999, 1691.
35. (d) Timmons, D. J.; Doyle, M. P. J. Organomet. Chem. 2001, 617, 98.
36. (e) Doyle, M. P.; Hu, W. Tetrahedron Lett. 2000, 41, 6265.
37. (f) Doyle, M. P.; Hu, W. H. Synlett 2001, 1364.
38. (g) Imogai, H.; Bernardinelli, G.; Granicher, C.; Moran, M.; Rossier, J. G.; Muller, P. Helv. Chim. Acta 1998, 87, 1754.
39. (a) Liao, L.-a.; Zhang, F.; Yan, N.; Golen, J. A.; Fox, J. M. Tetradedron 2004, 60, 1803.
40. (b) Liao, L.-a.; Zhang, F.; Dmitrenko, O.; Bach, R. D.; Fox, J. M. J. Am. Chem. Soc. 2004, 126, 4490.
41. (c) Fox, J. M.; Dmitrenko, O.; Liao, L.-a.; Bach, R. D. J. Org. Chem. 2004, 69, 7317.
42. Davies, H. M. L.; Lee, G. H. Org. Lett. 2004, 6, 1233.
43. For a recent modification of the Doyle, Müller, Shapiro cyclopropenation system, see: Luo, Y.; Horikawa, M.; Kloster, R. A.; Hawryluk, N. A.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8916.
44. In analogy to the common nomenclature of alkynes, we refer to cyclopropenes with a single alkene substituent as "terminal" cyclopropenes and to those with two alkene substitutents as "internal" cyclopropenes. To our knowledge, there are only two examples of resolutions for "internal" cyclopropenes. See ref 7a and Arrowood, T. L.; Kass, S. R. J. Am. Chem. Soc. 1999, 121, 7272.
45. Fattahi, A.; McCarthy, R. E.; Ahmad, M. R.; Kass, S. R. J. Am. Chem. Soc. 2003, 125, 11746 and references therein.
46. Early examples of cyclopropene deprotonation/alkylation or deprotonation/silylation: see ref 4 and (a) Closs, G. L.; Closs, L. E. J. Am. Chem. Soc. 1963, 85, 99. (b) Avezov, I. B.; Bolesov, I. G.; Levina, R. Y. J. Org. Chem. (USSR), Engl. Trans. 1974, 10, 2129. (c) Isaka, M.; Matsuzawa, S.; Yamago, S.; Ejiri, S.; Miyachi, Y.; Nakamura, E. J. Org. Chem. 1989, 54, 4727. (d) Kirms, M. A.; Primke, H.; Stohlmeier, M.; de Meijere, A. Recl. Trav. Chim. Pays-Bas. 1986, 105, 462. (e) Schipperijn, A. J.; Smael, P. Recl. Trav. Chim. Pays-Bas. 1973, 92, 1159.
47. Early examples of cyclopropene deprotonation/alkylation or deprotonation/silylation: see ref 4 and (a) Closs, G. L.; Closs, L. E. J. Am. Chem. Soc. 1963, 85, 99. (b) Avezov, I. B.; Bolesov, I. G.; Levina, R. Y. J. Org. Chem. (USSR), Engl. Trans. 1974, 10, 2129. (c) Isaka, M.; Matsuzawa, S.; Yamago, S.; Ejiri, S.; Miyachi, Y.; Nakamura, E. J. Org. Chem. 1989, 54, 4727. (d) Kirms, M. A.; Primke, H.; Stohlmeier, M.; de Meijere, A. Recl. Trav. Chim. Pays-Bas. 1986, 105, 462. (e) Schipperijn, A. J.; Smael, P. Recl. Trav. Chim. Pays-Bas. 1973, 92, 1159.
48. Early examples of cyclopropene deprotonation/alkylation or deprotonation/silylation: see ref 4 and (a) Closs, G. L.; Closs, L. E. J. Am. Chem. Soc. 1963, 85, 99. (b) Avezov, I. B.; Bolesov, I. G.; Levina, R. Y. J. Org. Chem. (USSR), Engl. Trans. 1974, 10, 2129. (c) Isaka, M.; Matsuzawa, S.; Yamago, S.; Ejiri, S.; Miyachi, Y.; Nakamura, E. J. Org. Chem. 1989, 54, 4727. (d) Kirms, M. A.; Primke, H.; Stohlmeier, M.; de Meijere, A. Recl. Trav. Chim. Pays-Bas. 1986, 105, 462. (e) Schipperijn, A. J.; Smael, P. Recl. Trav. Chim. Pays-Bas. 1973, 92, 1159.
49. Early examples of cyclopropene deprotonation/alkylation or deprotonation/silylation: see ref 4 and (a) Closs, G. L.; Closs, L. E. J. Am. Chem. Soc. 1963, 85, 99. (b) Avezov, I. B.; Bolesov, I. G.; Levina, R. Y. J. Org. Chem. (USSR), Engl. Trans. 1974, 10, 2129. (c) Isaka, M.; Matsuzawa, S.; Yamago, S.; Ejiri, S.; Miyachi, Y.; Nakamura, E. J. Org. Chem. 1989, 54, 4727. (d) Kirms, M. A.; Primke, H.; Stohlmeier, M.; de Meijere, A. Recl. Trav. Chim. Pays-Bas. 1986, 105, 462. (e) Schipperijn, A. J.; Smael, P. Recl. Trav. Chim. Pays-Bas. 1973, 92, 1159.
50. Early examples of cyclopropene deprotonation/alkylation or deprotonation/silylation: see ref 4 and (a) Closs, G. L.; Closs, L. E. J. Am. Chem. Soc. 1963, 85, 99. (b) Avezov, I. B.; Bolesov, I. G.; Levina, R. Y. J. Org. Chem. (USSR), Engl. Trans. 1974, 10, 2129. (c) Isaka, M.; Matsuzawa, S.; Yamago, S.; Ejiri, S.; Miyachi, Y.; Nakamura, E. J. Org. Chem. 1989, 54, 4727. (d) Kirms, M. A.; Primke, H.; Stohlmeier, M.; de Meijere, A. Recl. Trav. Chim. Pays-Bas. 1986, 105, 462. (e) Schipperijn, A. J.; Smael, P. Recl. Trav. Chim. Pays-Bas. 1973, 92, 1159.
51. Cyclopropene deprotonation/cross-coupling: see refs 4, 12c and (a) Grüger, G.; Szeimies, G. Tetrahedron Lett. 1986, 27, 1563. (b) Unteidt, S.; de Meijere, A. Chem. Ber. 1994, 127, 1511.
52. Cyclopropene deprotonation/cross-coupling: see refs 4, 12c and (a) Grüger, G.; Szeimies, G. Tetrahedron Lett. 1986, 27, 1563. (b) Unteidt, S.; de Meijere, A. Chem. Ber. 1994, 127, 1511.
53. (a) Zrinski, I.; Novak-Coumbassa, N.; Eckert-Maksic, M. Organometallics 2004, 23, 2806.
54. (b) Zrinski, I.; Eckert-Maksic, M. Synth. Commun. 2003, 33, 4071.
55. (c) Zrinski, I.; Gadanji, G.; Eckert-Maksic, M. New J. Chem, 2003, 27, 1270.