Synthesis of 3-hexahelicenol and its transformation to 3-hexahelicenylamines, diphenylphosphine, methyl carboxylate, and dimethylthiocarbamate

Journal of Organic Chemistry

Volumn 68, Issue 13, 2003, Pages 5193-5197

  Teplý, Filip ^a   Stará, Irena G ^a   Starý, Ivo ^a   Kollárovič, Adrian ^a   Šaman, David ^a   Vyskočil, Štěpán ^b   Fiedler, Pavel ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; ISOMERIZATION; NAPHTHALENE; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CYCLOISOMERIZATION;

AMINES;

1 BROMO 2 (BROMOMETHYL)NAPHTHALENE; 1 METHOXY 3 METHYLBENZENE; 3 HEXAHELICENOL; 3 HEXAHELICENYLAMINE; BENZENE DERIVATIVE; CARBAMIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CARBOXYLIC ACID METHYL ESTER; DIMETHYLTHIOCARBAMATE; DIPHENYLPHOSPHINE; NAPHTHALENE DERIVATIVE; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ISOMERISM; SYNTHESIS;

EID: 0037534103     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034369t     Document Type: Article

References (70)

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12. For alcohols and their derivatives, see: (a) Ogawa, Y.; Toyama, M.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2003, 44, 2167. (b) Ogawa, Y.; Ueno, T.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2002, 43, 7827. (c) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. (d) Paruch, K.; Vyklický, L.; Katz, T. J.; Incarvito, C. D.; Rheingold, A. L. J. Org. Chem. 2000, 65, 8774. (e) Thongpanchang, T.; Paruch, K.; Katz, T. J.; Rheingold, A. L.; Lam, K.-C.; Liable-Sands, L. J. Org. Chem. 2000, 65, 1850. (f) Dreher, S. D.; Paruch, K.; Katz, T. J. J. Org. Chem. 2000, 65, 806. (g) Meier, H.; Schwertel, M.; Schollmeyer, D. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 2000, 56, 684. (h) Nuckolls, C.; Katz, T. J.; Katz, G.; Collings, P. J.; Castellanos, L. J. Am. Chem. Soc. 1999, 121, 79. (i) Meier, H.; Schwertel, M.; Schollmeyer, D. Angew. Chem., Int. Ed. 1998, 37, 2110. (j) Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. (k) Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. (l) Nuckolls, C.; Katz, T. J.; Castellanos, L. J. Am. Chem. Soc. 1996, 118, 3767. (m) Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem. 1996, 108, 2230. (n) Yang, B.; Liu, L.; Katz, T. J.; Liberko, C. A.; Miller, L. L. J. Am. Chem. Soc. 1991, 113, 8993. (o) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (p) Brown, J. M.; Field, I. P.; Sidebottom, P. J. Tetrahedron Lett. 1981, 22, 4867.
13. For alcohols and their derivatives, see: (a) Ogawa, Y.; Toyama, M.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2003, 44, 2167. (b) Ogawa, Y.; Ueno, T.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2002, 43, 7827. (c) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. (d) Paruch, K.; Vyklický, L.; Katz, T. J.; Incarvito, C. D.; Rheingold, A. L. J. Org. Chem. 2000, 65, 8774. (e) Thongpanchang, T.; Paruch, K.; Katz, T. J.; Rheingold, A. L.; Lam, K.-C.; Liable-Sands, L. J. Org. Chem. 2000, 65, 1850. (f) Dreher, S. D.; Paruch, K.; Katz, T. J. J. Org. Chem. 2000, 65, 806. (g) Meier, H.; Schwertel, M.; Schollmeyer, D. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 2000, 56, 684. (h) Nuckolls, C.; Katz, T. J.; Katz, G.; Collings, P. J.; Castellanos, L. J. Am. Chem. Soc. 1999, 121, 79. (i) Meier, H.; Schwertel, M.; Schollmeyer, D. Angew. Chem., Int. Ed. 1998, 37, 2110. (j) Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. (k) Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. (l) Nuckolls, C.; Katz, T. J.; Castellanos, L. J. Am. Chem. Soc. 1996, 118, 3767. (m) Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem. 1996, 108, 2230. (n) Yang, B.; Liu, L.; Katz, T. J.; Liberko, C. A.; Miller, L. L. J. Am. Chem. Soc. 1991, 113, 8993. (o) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (p) Brown, J. M.; Field, I. P.; Sidebottom, P. J. Tetrahedron Lett. 1981, 22, 4867.
14. For alcohols and their derivatives, see: (a) Ogawa, Y.; Toyama, M.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2003, 44, 2167. (b) Ogawa, Y.; Ueno, T.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2002, 43, 7827. (c) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. (d) Paruch, K.; Vyklický, L.; Katz, T. J.; Incarvito, C. D.; Rheingold, A. L. J. Org. Chem. 2000, 65, 8774. (e) Thongpanchang, T.; Paruch, K.; Katz, T. J.; Rheingold, A. L.; Lam, K.-C.; Liable-Sands, L. J. Org. Chem. 2000, 65, 1850. (f) Dreher, S. D.; Paruch, K.; Katz, T. J. J. Org. Chem. 2000, 65, 806. (g) Meier, H.; Schwertel, M.; Schollmeyer, D. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 2000, 56, 684. (h) Nuckolls, C.; Katz, T. J.; Katz, G.; Collings, P. J.; Castellanos, L. J. Am. Chem. Soc. 1999, 121, 79. (i) Meier, H.; Schwertel, M.; Schollmeyer, D. Angew. Chem., Int. Ed. 1998, 37, 2110. (j) Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. (k) Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. (l) Nuckolls, C.; Katz, T. J.; Castellanos, L. J. Am. Chem. Soc. 1996, 118, 3767. (m) Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem. 1996, 108, 2230. (n) Yang, B.; Liu, L.; Katz, T. J.; Liberko, C. A.; Miller, L. L. J. Am. Chem. Soc. 1991, 113, 8993. (o) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (p) Brown, J. M.; Field, I. P.; Sidebottom, P. J. Tetrahedron Lett. 1981, 22, 4867.
15. For alcohols and their derivatives, see: (a) Ogawa, Y.; Toyama, M.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2003, 44, 2167. (b) Ogawa, Y.; Ueno, T.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2002, 43, 7827. (c) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. (d) Paruch, K.; Vyklický, L.; Katz, T. J.; Incarvito, C. D.; Rheingold, A. L. J. Org. Chem. 2000, 65, 8774. (e) Thongpanchang, T.; Paruch, K.; Katz, T. J.; Rheingold, A. L.; Lam, K.-C.; Liable-Sands, L. J. Org. Chem. 2000, 65, 1850. (f) Dreher, S. D.; Paruch, K.; Katz, T. J. J. Org. Chem. 2000, 65, 806. (g) Meier, H.; Schwertel, M.; Schollmeyer, D. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 2000, 56, 684. (h) Nuckolls, C.; Katz, T. J.; Katz, G.; Collings, P. J.; Castellanos, L. J. Am. Chem. Soc. 1999, 121, 79. (i) Meier, H.; Schwertel, M.; Schollmeyer, D. Angew. Chem., Int. Ed. 1998, 37, 2110. (j) Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. (k) Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. (l) Nuckolls, C.; Katz, T. J.; Castellanos, L. J. Am. Chem. Soc. 1996, 118, 3767. (m) Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem. 1996, 108, 2230. (n) Yang, B.; Liu, L.; Katz, T. J.; Liberko, C. A.; Miller, L. L. J. Am. Chem. Soc. 1991, 113, 8993. (o) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (p) Brown, J. M.; Field, I. P.; Sidebottom, P. J. Tetrahedron Lett. 1981, 22, 4867.
16. For alcohols and their derivatives, see: (a) Ogawa, Y.; Toyama, M.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2003, 44, 2167. (b) Ogawa, Y.; Ueno, T.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2002, 43, 7827. (c) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. (d) Paruch, K.; Vyklický, L.; Katz, T. J.; Incarvito, C. D.; Rheingold, A. L. J. Org. Chem. 2000, 65, 8774. (e) Thongpanchang, T.; Paruch, K.; Katz, T. J.; Rheingold, A. L.; Lam, K.-C.; Liable-Sands, L. J. Org. Chem. 2000, 65, 1850. (f) Dreher, S. D.; Paruch, K.; Katz, T. J. J. Org. Chem. 2000, 65, 806. (g) Meier, H.; Schwertel, M.; Schollmeyer, D. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 2000, 56, 684. (h) Nuckolls, C.; Katz, T. J.; Katz, G.; Collings, P. J.; Castellanos, L. J. Am. Chem. Soc. 1999, 121, 79. (i) Meier, H.; Schwertel, M.; Schollmeyer, D. Angew. Chem., Int. Ed. 1998, 37, 2110. (j) Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. (k) Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. (l) Nuckolls, C.; Katz, T. J.; Castellanos, L. J. Am. Chem. Soc. 1996, 118, 3767. (m) Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem. 1996, 108, 2230. (n) Yang, B.; Liu, L.; Katz, T. J.; Liberko, C. A.; Miller, L. L. J. Am. Chem. Soc. 1991, 113, 8993. (o) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (p) Brown, J. M.; Field, I. P.; Sidebottom, P. J. Tetrahedron Lett. 1981, 22, 4867.
17. For alcohols and their derivatives, see: (a) Ogawa, Y.; Toyama, M.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2003, 44, 2167. (b) Ogawa, Y.; Ueno, T.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2002, 43, 7827. (c) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. (d) Paruch, K.; Vyklický, L.; Katz, T. J.; Incarvito, C. D.; Rheingold, A. L. J. Org. Chem. 2000, 65, 8774. (e) Thongpanchang, T.; Paruch, K.; Katz, T. J.; Rheingold, A. L.; Lam, K.-C.; Liable-Sands, L. J. Org. Chem. 2000, 65, 1850. (f) Dreher, S. D.; Paruch, K.; Katz, T. J. J. Org. Chem. 2000, 65, 806. (g) Meier, H.; Schwertel, M.; Schollmeyer, D. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 2000, 56, 684. (h) Nuckolls, C.; Katz, T. J.; Katz, G.; Collings, P. J.; Castellanos, L. J. Am. Chem. Soc. 1999, 121, 79. (i) Meier, H.; Schwertel, M.; Schollmeyer, D. Angew. Chem., Int. Ed. 1998, 37, 2110. (j) Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. (k) Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. (l) Nuckolls, C.; Katz, T. J.; Castellanos, L. J. Am. Chem. Soc. 1996, 118, 3767. (m) Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem. 1996, 108, 2230. (n) Yang, B.; Liu, L.; Katz, T. J.; Liberko, C. A.; Miller, L. L. J. Am. Chem. Soc. 1991, 113, 8993. (o) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (p) Brown, J. M.; Field, I. P.; Sidebottom, P. J. Tetrahedron Lett. 1981, 22, 4867.
18. For alcohols and their derivatives, see: (a) Ogawa, Y.; Toyama, M.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2003, 44, 2167. (b) Ogawa, Y.; Ueno, T.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2002, 43, 7827. (c) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. (d) Paruch, K.; Vyklický, L.; Katz, T. J.; Incarvito, C. D.; Rheingold, A. L. J. Org. Chem. 2000, 65, 8774. (e) Thongpanchang, T.; Paruch, K.; Katz, T. J.; Rheingold, A. L.; Lam, K.-C.; Liable-Sands, L. J. Org. Chem. 2000, 65, 1850. (f) Dreher, S. D.; Paruch, K.; Katz, T. J. J. Org. Chem. 2000, 65, 806. (g) Meier, H.; Schwertel, M.; Schollmeyer, D. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 2000, 56, 684. (h) Nuckolls, C.; Katz, T. J.; Katz, G.; Collings, P. J.; Castellanos, L. J. Am. Chem. Soc. 1999, 121, 79. (i) Meier, H.; Schwertel, M.; Schollmeyer, D. Angew. Chem., Int. Ed. 1998, 37, 2110. (j) Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. (k) Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. (l) Nuckolls, C.; Katz, T. J.; Castellanos, L. J. Am. Chem. Soc. 1996, 118, 3767. (m) Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem. 1996, 108, 2230. (n) Yang, B.; Liu, L.; Katz, T. J.; Liberko, C. A.; Miller, L. L. J. Am. Chem. Soc. 1991, 113, 8993. (o) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (p) Brown, J. M.; Field, I. P.; Sidebottom, P. J. Tetrahedron Lett. 1981, 22, 4867.
19. For alcohols and their derivatives, see: (a) Ogawa, Y.; Toyama, M.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2003, 44, 2167. (b) Ogawa, Y.; Ueno, T.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2002, 43, 7827. (c) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. (d) Paruch, K.; Vyklický, L.; Katz, T. J.; Incarvito, C. D.; Rheingold, A. L. J. Org. Chem. 2000, 65, 8774. (e) Thongpanchang, T.; Paruch, K.; Katz, T. J.; Rheingold, A. L.; Lam, K.-C.; Liable-Sands, L. J. Org. Chem. 2000, 65, 1850. (f) Dreher, S. D.; Paruch, K.; Katz, T. J. J. Org. Chem. 2000, 65, 806. (g) Meier, H.; Schwertel, M.; Schollmeyer, D. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 2000, 56, 684. (h) Nuckolls, C.; Katz, T. J.; Katz, G.; Collings, P. J.; Castellanos, L. J. Am. Chem. Soc. 1999, 121, 79. (i) Meier, H.; Schwertel, M.; Schollmeyer, D. Angew. Chem., Int. Ed. 1998, 37, 2110. (j) Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. (k) Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. (l) Nuckolls, C.; Katz, T. J.; Castellanos, L. J. Am. Chem. Soc. 1996, 118, 3767. (m) Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem. 1996, 108, 2230. (n) Yang, B.; Liu, L.; Katz, T. J.; Liberko, C. A.; Miller, L. L. J. Am. Chem. Soc. 1991, 113, 8993. (o) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (p) Brown, J. M.; Field, I. P.; Sidebottom, P. J. Tetrahedron Lett. 1981, 22, 4867.
20. For alcohols and their derivatives, see: (a) Ogawa, Y.; Toyama, M.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2003, 44, 2167. (b) Ogawa, Y.; Ueno, T.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2002, 43, 7827. (c) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. (d) Paruch, K.; Vyklický, L.; Katz, T. J.; Incarvito, C. D.; Rheingold, A. L. J. Org. Chem. 2000, 65, 8774. (e) Thongpanchang, T.; Paruch, K.; Katz, T. J.; Rheingold, A. L.; Lam, K.-C.; Liable-Sands, L. J. Org. Chem. 2000, 65, 1850. (f) Dreher, S. D.; Paruch, K.; Katz, T. J. J. Org. Chem. 2000, 65, 806. (g) Meier, H.; Schwertel, M.; Schollmeyer, D. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 2000, 56, 684. (h) Nuckolls, C.; Katz, T. J.; Katz, G.; Collings, P. J.; Castellanos, L. J. Am. Chem. Soc. 1999, 121, 79. (i) Meier, H.; Schwertel, M.; Schollmeyer, D. Angew. Chem., Int. Ed. 1998, 37, 2110. (j) Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. (k) Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. (l) Nuckolls, C.; Katz, T. J.; Castellanos, L. J. Am. Chem. Soc. 1996, 118, 3767. (m) Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem. 1996, 108, 2230. (n) Yang, B.; Liu, L.; Katz, T. J.; Liberko, C. A.; Miller, L. L. J. Am. Chem. Soc. 1991, 113, 8993. (o) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (p) Brown, J. M.; Field, I. P.; Sidebottom, P. J. Tetrahedron Lett. 1981, 22, 4867.
21. For alcohols and their derivatives, see: (a) Ogawa, Y.; Toyama, M.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2003, 44, 2167. (b) Ogawa, Y.; Ueno, T.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2002, 43, 7827. (c) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. (d) Paruch, K.; Vyklický, L.; Katz, T. J.; Incarvito, C. D.; Rheingold, A. L. J. Org. Chem. 2000, 65, 8774. (e) Thongpanchang, T.; Paruch, K.; Katz, T. J.; Rheingold, A. L.; Lam, K.-C.; Liable-Sands, L. J. Org. Chem. 2000, 65, 1850. (f) Dreher, S. D.; Paruch, K.; Katz, T. J. J. Org. Chem. 2000, 65, 806. (g) Meier, H.; Schwertel, M.; Schollmeyer, D. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 2000, 56, 684. (h) Nuckolls, C.; Katz, T. J.; Katz, G.; Collings, P. J.; Castellanos, L. J. Am. Chem. Soc. 1999, 121, 79. (i) Meier, H.; Schwertel, M.; Schollmeyer, D. Angew. Chem., Int. Ed. 1998, 37, 2110. (j) Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. (k) Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. (l) Nuckolls, C.; Katz, T. J.; Castellanos, L. J. Am. Chem. Soc. 1996, 118, 3767. (m) Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem. 1996, 108, 2230. (n) Yang, B.; Liu, L.; Katz, T. J.; Liberko, C. A.; Miller, L. L. J. Am. Chem. Soc. 1991, 113, 8993. (o) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (p) Brown, J. M.; Field, I. P.; Sidebottom, P. J. Tetrahedron Lett. 1981, 22, 4867.
22. For alcohols and their derivatives, see: (a) Ogawa, Y.; Toyama, M.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2003, 44, 2167. (b) Ogawa, Y.; Ueno, T.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2002, 43, 7827. (c) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. (d) Paruch, K.; Vyklický, L.; Katz, T. J.; Incarvito, C. D.; Rheingold, A. L. J. Org. Chem. 2000, 65, 8774. (e) Thongpanchang, T.; Paruch, K.; Katz, T. J.; Rheingold, A. L.; Lam, K.-C.; Liable-Sands, L. J. Org. Chem. 2000, 65, 1850. (f) Dreher, S. D.; Paruch, K.; Katz, T. J. J. Org. Chem. 2000, 65, 806. (g) Meier, H.; Schwertel, M.; Schollmeyer, D. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 2000, 56, 684. (h) Nuckolls, C.; Katz, T. J.; Katz, G.; Collings, P. J.; Castellanos, L. J. Am. Chem. Soc. 1999, 121, 79. (i) Meier, H.; Schwertel, M.; Schollmeyer, D. Angew. Chem., Int. Ed. 1998, 37, 2110. (j) Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. (k) Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. (l) Nuckolls, C.; Katz, T. J.; Castellanos, L. J. Am. Chem. Soc. 1996, 118, 3767. (m) Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem. 1996, 108, 2230. (n) Yang, B.; Liu, L.; Katz, T. J.; Liberko, C. A.; Miller, L. L. J. Am. Chem. Soc. 1991, 113, 8993. (o) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (p) Brown, J. M.; Field, I. P.; Sidebottom, P. J. Tetrahedron Lett. 1981, 22, 4867.
23. For alcohols and their derivatives, see: (a) Ogawa, Y.; Toyama, M.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2003, 44, 2167. (b) Ogawa, Y.; Ueno, T.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2002, 43, 7827. (c) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. (d) Paruch, K.; Vyklický, L.; Katz, T. J.; Incarvito, C. D.; Rheingold, A. L. J. Org. Chem. 2000, 65, 8774. (e) Thongpanchang, T.; Paruch, K.; Katz, T. J.; Rheingold, A. L.; Lam, K.-C.; Liable-Sands, L. J. Org. Chem. 2000, 65, 1850. (f) Dreher, S. D.; Paruch, K.; Katz, T. J. J. Org. Chem. 2000, 65, 806. (g) Meier, H.; Schwertel, M.; Schollmeyer, D. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 2000, 56, 684. (h) Nuckolls, C.; Katz, T. J.; Katz, G.; Collings, P. J.; Castellanos, L. J. Am. Chem. Soc. 1999, 121, 79. (i) Meier, H.; Schwertel, M.; Schollmeyer, D. Angew. Chem., Int. Ed. 1998, 37, 2110. (j) Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. (k) Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. (l) Nuckolls, C.; Katz, T. J.; Castellanos, L. J. Am. Chem. Soc. 1996, 118, 3767. (m) Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem. 1996, 108, 2230. (n) Yang, B.; Liu, L.; Katz, T. J.; Liberko, C. A.; Miller, L. L. J. Am. Chem. Soc. 1991, 113, 8993. (o) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (p) Brown, J. M.; Field, I. P.; Sidebottom, P. J. Tetrahedron Lett. 1981, 22, 4867.
24. For alcohols and their derivatives, see: (a) Ogawa, Y.; Toyama, M.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2003, 44, 2167. (b) Ogawa, Y.; Ueno, T.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2002, 43, 7827. (c) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. (d) Paruch, K.; Vyklický, L.; Katz, T. J.; Incarvito, C. D.; Rheingold, A. L. J. Org. Chem. 2000, 65, 8774. (e) Thongpanchang, T.; Paruch, K.; Katz, T. J.; Rheingold, A. L.; Lam, K.-C.; Liable-Sands, L. J. Org. Chem. 2000, 65, 1850. (f) Dreher, S. D.; Paruch, K.; Katz, T. J. J. Org. Chem. 2000, 65, 806. (g) Meier, H.; Schwertel, M.; Schollmeyer, D. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 2000, 56, 684. (h) Nuckolls, C.; Katz, T. J.; Katz, G.; Collings, P. J.; Castellanos, L. J. Am. Chem. Soc. 1999, 121, 79. (i) Meier, H.; Schwertel, M.; Schollmeyer, D. Angew. Chem., Int. Ed. 1998, 37, 2110. (j) Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. (k) Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. (l) Nuckolls, C.; Katz, T. J.; Castellanos, L. J. Am. Chem. Soc. 1996, 118, 3767. (m) Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem. 1996, 108, 2230. (n) Yang, B.; Liu, L.; Katz, T. J.; Liberko, C. A.; Miller, L. L. J. Am. Chem. Soc. 1991, 113, 8993. (o) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (p) Brown, J. M.; Field, I. P.; Sidebottom, P. J. Tetrahedron Lett. 1981, 22, 4867.
25. For alcohols and their derivatives, see: (a) Ogawa, Y.; Toyama, M.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2003, 44, 2167. (b) Ogawa, Y.; Ueno, T.; Karikomi, M.; Seki, K.; Haga, K.; Uyehara, T. Tetrahedron Lett. 2002, 43, 7827. (c) Reetz, M. T.; Sostmann, S. Tetrahedron 2001, 57, 2515. (d) Paruch, K.; Vyklický, L.; Katz, T. J.; Incarvito, C. D.; Rheingold, A. L. J. Org. Chem. 2000, 65, 8774. (e) Thongpanchang, T.; Paruch, K.; Katz, T. J.; Rheingold, A. L.; Lam, K.-C.; Liable-Sands, L. J. Org. Chem. 2000, 65, 1850. (f) Dreher, S. D.; Paruch, K.; Katz, T. J. J. Org. Chem. 2000, 65, 806. (g) Meier, H.; Schwertel, M.; Schollmeyer, D. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 2000, 56, 684. (h) Nuckolls, C.; Katz, T. J.; Katz, G.; Collings, P. J.; Castellanos, L. J. Am. Chem. Soc. 1999, 121, 79. (i) Meier, H.; Schwertel, M.; Schollmeyer, D. Angew. Chem., Int. Ed. 1998, 37, 2110. (j) Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. (k) Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. (l) Nuckolls, C.; Katz, T. J.; Castellanos, L. J. Am. Chem. Soc. 1996, 118, 3767. (m) Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem. 1996, 108, 2230. (n) Yang, B.; Liu, L.; Katz, T. J.; Liberko, C. A.; Miller, L. L. J. Am. Chem. Soc. 1991, 113, 8993. (o) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (p) Brown, J. M.; Field, I. P.; Sidebottom, P. J. Tetrahedron Lett. 1981, 22, 4867.
26. For carboxylic acids and their derivatives, see: (a) Fox, J. M.; Lin, D.; Itagaki, Y.; Fujita, T. J. Org. Chem. 1998, 63, 2031. (b) Janke, R.; Haufe, G. Zh. Org. Khim. 1994, 30, 1365. (c) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (d) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 547. (e) Gorsane, M.; Defay, N.; Martin, R. H. Bull. Soc. Chim. Belg. 1985, 94, 215. (f) Kim, Y. H.; Balan, A.; Tishbee, A.; Gil-Av, E. J. Chem. Soc., Chem. Commun. 1982, 1336. (g) Balan, A.; Gottlieb, H. E. J. Chem. Soc., Perkin Trans. 2 1981, 350. (h) Martin, R. H.; Libert, V. J. Chem. Res. Miniprint 1980, 4, 1940. (i) Cochez, Y.; Martin, R. H.; Jespers, J. Isr. J. Chem. 1976, 15, 29. (j) Jutz, C.; Loebering, H.-G. Angew. Chem. 1975, 87, 415. (k) Martin, R. H. Chimia 1975, 29, 137. (l) Martin, R. H.; Cosyn, J. P. Synth. Commun. 1971, 1, 257.
27. For carboxylic acids and their derivatives, see: (a) Fox, J. M.; Lin, D.; Itagaki, Y.; Fujita, T. J. Org. Chem. 1998, 63, 2031. (b) Janke, R.; Haufe, G. Zh. Org. Khim. 1994, 30, 1365. (c) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (d) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 547. (e) Gorsane, M.; Defay, N.; Martin, R. H. Bull. Soc. Chim. Belg. 1985, 94, 215. (f) Kim, Y. H.; Balan, A.; Tishbee, A.; Gil-Av, E. J. Chem. Soc., Chem. Commun. 1982, 1336. (g) Balan, A.; Gottlieb, H. E. J. Chem. Soc., Perkin Trans. 2 1981, 350. (h) Martin, R. H.; Libert, V. J. Chem. Res. Miniprint 1980, 4, 1940. (i) Cochez, Y.; Martin, R. H.; Jespers, J. Isr. J. Chem. 1976, 15, 29. (j) Jutz, C.; Loebering, H.-G. Angew. Chem. 1975, 87, 415. (k) Martin, R. H. Chimia 1975, 29, 137. (l) Martin, R. H.; Cosyn, J. P. Synth. Commun. 1971, 1, 257.
28. For carboxylic acids and their derivatives, see: (a) Fox, J. M.; Lin, D.; Itagaki, Y.; Fujita, T. J. Org. Chem. 1998, 63, 2031. (b) Janke, R.; Haufe, G. Zh. Org. Khim. 1994, 30, 1365. (c) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (d) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 547. (e) Gorsane, M.; Defay, N.; Martin, R. H. Bull. Soc. Chim. Belg. 1985, 94, 215. (f) Kim, Y. H.; Balan, A.; Tishbee, A.; Gil-Av, E. J. Chem. Soc., Chem. Commun. 1982, 1336. (g) Balan, A.; Gottlieb, H. E. J. Chem. Soc., Perkin Trans. 2 1981, 350. (h) Martin, R. H.; Libert, V. J. Chem. Res. Miniprint 1980, 4, 1940. (i) Cochez, Y.; Martin, R. H.; Jespers, J. Isr. J. Chem. 1976, 15, 29. (j) Jutz, C.; Loebering, H.-G. Angew. Chem. 1975, 87, 415. (k) Martin, R. H. Chimia 1975, 29, 137. (l) Martin, R. H.; Cosyn, J. P. Synth. Commun. 1971, 1, 257.
29. For carboxylic acids and their derivatives, see: (a) Fox, J. M.; Lin, D.; Itagaki, Y.; Fujita, T. J. Org. Chem. 1998, 63, 2031. (b) Janke, R.; Haufe, G. Zh. Org. Khim. 1994, 30, 1365. (c) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (d) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 547. (e) Gorsane, M.; Defay, N.; Martin, R. H. Bull. Soc. Chim. Belg. 1985, 94, 215. (f) Kim, Y. H.; Balan, A.; Tishbee, A.; Gil-Av, E. J. Chem. Soc., Chem. Commun. 1982, 1336. (g) Balan, A.; Gottlieb, H. E. J. Chem. Soc., Perkin Trans. 2 1981, 350. (h) Martin, R. H.; Libert, V. J. Chem. Res. Miniprint 1980, 4, 1940. (i) Cochez, Y.; Martin, R. H.; Jespers, J. Isr. J. Chem. 1976, 15, 29. (j) Jutz, C.; Loebering, H.-G. Angew. Chem. 1975, 87, 415. (k) Martin, R. H. Chimia 1975, 29, 137. (l) Martin, R. H.; Cosyn, J. P. Synth. Commun. 1971, 1, 257.
30. For carboxylic acids and their derivatives, see: (a) Fox, J. M.; Lin, D.; Itagaki, Y.; Fujita, T. J. Org. Chem. 1998, 63, 2031. (b) Janke, R.; Haufe, G. Zh. Org. Khim. 1994, 30, 1365. (c) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (d) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 547. (e) Gorsane, M.; Defay, N.; Martin, R. H. Bull. Soc. Chim. Belg. 1985, 94, 215. (f) Kim, Y. H.; Balan, A.; Tishbee, A.; Gil-Av, E. J. Chem. Soc., Chem. Commun. 1982, 1336. (g) Balan, A.; Gottlieb, H. E. J. Chem. Soc., Perkin Trans. 2 1981, 350. (h) Martin, R. H.; Libert, V. J. Chem. Res. Miniprint 1980, 4, 1940. (i) Cochez, Y.; Martin, R. H.; Jespers, J. Isr. J. Chem. 1976, 15, 29. (j) Jutz, C.; Loebering, H.-G. Angew. Chem. 1975, 87, 415. (k) Martin, R. H. Chimia 1975, 29, 137. (l) Martin, R. H.; Cosyn, J. P. Synth. Commun. 1971, 1, 257.
31. For carboxylic acids and their derivatives, see: (a) Fox, J. M.; Lin, D.; Itagaki, Y.; Fujita, T. J. Org. Chem. 1998, 63, 2031. (b) Janke, R.; Haufe, G. Zh. Org. Khim. 1994, 30, 1365. (c) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (d) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 547. (e) Gorsane, M.; Defay, N.; Martin, R. H. Bull. Soc. Chim. Belg. 1985, 94, 215. (f) Kim, Y. H.; Balan, A.; Tishbee, A.; Gil-Av, E. J. Chem. Soc., Chem. Commun. 1982, 1336. (g) Balan, A.; Gottlieb, H. E. J. Chem. Soc., Perkin Trans. 2 1981, 350. (h) Martin, R. H.; Libert, V. J. Chem. Res. Miniprint 1980, 4, 1940. (i) Cochez, Y.; Martin, R. H.; Jespers, J. Isr. J. Chem. 1976, 15, 29. (j) Jutz, C.; Loebering, H.-G. Angew. Chem. 1975, 87, 415. (k) Martin, R. H. Chimia 1975, 29, 137. (l) Martin, R. H.; Cosyn, J. P. Synth. Commun. 1971, 1, 257.
32. For carboxylic acids and their derivatives, see: (a) Fox, J. M.; Lin, D.; Itagaki, Y.; Fujita, T. J. Org. Chem. 1998, 63, 2031. (b) Janke, R.; Haufe, G. Zh. Org. Khim. 1994, 30, 1365. (c) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (d) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 547. (e) Gorsane, M.; Defay, N.; Martin, R. H. Bull. Soc. Chim. Belg. 1985, 94, 215. (f) Kim, Y. H.; Balan, A.; Tishbee, A.; Gil-Av, E. J. Chem. Soc., Chem. Commun. 1982, 1336. (g) Balan, A.; Gottlieb, H. E. J. Chem. Soc., Perkin Trans. 2 1981, 350. (h) Martin, R. H.; Libert, V. J. Chem. Res. Miniprint 1980, 4, 1940. (i) Cochez, Y.; Martin, R. H.; Jespers, J. Isr. J. Chem. 1976, 15, 29. (j) Jutz, C.; Loebering, H.-G. Angew. Chem. 1975, 87, 415. (k) Martin, R. H. Chimia 1975, 29, 137. (l) Martin, R. H.; Cosyn, J. P. Synth. Commun. 1971, 1, 257.
33. For carboxylic acids and their derivatives, see: (a) Fox, J. M.; Lin, D.; Itagaki, Y.; Fujita, T. J. Org. Chem. 1998, 63, 2031. (b) Janke, R.; Haufe, G. Zh. Org. Khim. 1994, 30, 1365. (c) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (d) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 547. (e) Gorsane, M.; Defay, N.; Martin, R. H. Bull. Soc. Chim. Belg. 1985, 94, 215. (f) Kim, Y. H.; Balan, A.; Tishbee, A.; Gil-Av, E. J. Chem. Soc., Chem. Commun. 1982, 1336. (g) Balan, A.; Gottlieb, H. E. J. Chem. Soc., Perkin Trans. 2 1981, 350. (h) Martin, R. H.; Libert, V. J. Chem. Res. Miniprint 1980, 4, 1940. (i) Cochez, Y.; Martin, R. H.; Jespers, J. Isr. J. Chem. 1976, 15, 29. (j) Jutz, C.; Loebering, H.-G. Angew. Chem. 1975, 87, 415. (k) Martin, R. H. Chimia 1975, 29, 137. (l) Martin, R. H.; Cosyn, J. P. Synth. Commun. 1971, 1, 257.
34. For carboxylic acids and their derivatives, see: (a) Fox, J. M.; Lin, D.; Itagaki, Y.; Fujita, T. J. Org. Chem. 1998, 63, 2031. (b) Janke, R.; Haufe, G. Zh. Org. Khim. 1994, 30, 1365. (c) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (d) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 547. (e) Gorsane, M.; Defay, N.; Martin, R. H. Bull. Soc. Chim. Belg. 1985, 94, 215. (f) Kim, Y. H.; Balan, A.; Tishbee, A.; Gil-Av, E. J. Chem. Soc., Chem. Commun. 1982, 1336. (g) Balan, A.; Gottlieb, H. E. J. Chem. Soc., Perkin Trans. 2 1981, 350. (h) Martin, R. H.; Libert, V. J. Chem. Res. Miniprint 1980, 4, 1940. (i) Cochez, Y.; Martin, R. H.; Jespers, J. Isr. J. Chem. 1976, 15, 29. (j) Jutz, C.; Loebering, H.-G. Angew. Chem. 1975, 87, 415. (k) Martin, R. H. Chimia 1975, 29, 137. (l) Martin, R. H.; Cosyn, J. P. Synth. Commun. 1971, 1, 257.
35. For carboxylic acids and their derivatives, see: (a) Fox, J. M.; Lin, D.; Itagaki, Y.; Fujita, T. J. Org. Chem. 1998, 63, 2031. (b) Janke, R.; Haufe, G. Zh. Org. Khim. 1994, 30, 1365. (c) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (d) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 547. (e) Gorsane, M.; Defay, N.; Martin, R. H. Bull. Soc. Chim. Belg. 1985, 94, 215. (f) Kim, Y. H.; Balan, A.; Tishbee, A.; Gil-Av, E. J. Chem. Soc., Chem. Commun. 1982, 1336. (g) Balan, A.; Gottlieb, H. E. J. Chem. Soc., Perkin Trans. 2 1981, 350. (h) Martin, R. H.; Libert, V. J. Chem. Res. Miniprint 1980, 4, 1940. (i) Cochez, Y.; Martin, R. H.; Jespers, J. Isr. J. Chem. 1976, 15, 29. (j) Jutz, C.; Loebering, H.-G. Angew. Chem. 1975, 87, 415. (k) Martin, R. H. Chimia 1975, 29, 137. (l) Martin, R. H.; Cosyn, J. P. Synth. Commun. 1971, 1, 257.
36. For carboxylic acids and their derivatives, see: (a) Fox, J. M.; Lin, D.; Itagaki, Y.; Fujita, T. J. Org. Chem. 1998, 63, 2031. (b) Janke, R.; Haufe, G. Zh. Org. Khim. 1994, 30, 1365. (c) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (d) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 547. (e) Gorsane, M.; Defay, N.; Martin, R. H. Bull. Soc. Chim. Belg. 1985, 94, 215. (f) Kim, Y. H.; Balan, A.; Tishbee, A.; Gil-Av, E. J. Chem. Soc., Chem. Commun. 1982, 1336. (g) Balan, A.; Gottlieb, H. E. J. Chem. Soc., Perkin Trans. 2 1981, 350. (h) Martin, R. H.; Libert, V. J. Chem. Res. Miniprint 1980, 4, 1940. (i) Cochez, Y.; Martin, R. H.; Jespers, J. Isr. J. Chem. 1976, 15, 29. (j) Jutz, C.; Loebering, H.-G. Angew. Chem. 1975, 87, 415. (k) Martin, R. H. Chimia 1975, 29, 137. (l) Martin, R. H.; Cosyn, J. P. Synth. Commun. 1971, 1, 257.
37. For carboxylic acids and their derivatives, see: (a) Fox, J. M.; Lin, D.; Itagaki, Y.; Fujita, T. J. Org. Chem. 1998, 63, 2031. (b) Janke, R.; Haufe, G. Zh. Org. Khim. 1994, 30, 1365. (c) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 557. (d) Hassine, B. B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 547. (e) Gorsane, M.; Defay, N.; Martin, R. H. Bull. Soc. Chim. Belg. 1985, 94, 215. (f) Kim, Y. H.; Balan, A.; Tishbee, A.; Gil-Av, E. J. Chem. Soc., Chem. Commun. 1982, 1336. (g) Balan, A.; Gottlieb, H. E. J. Chem. Soc., Perkin Trans. 2 1981, 350. (h) Martin, R. H.; Libert, V. J. Chem. Res. Miniprint 1980, 4, 1940. (i) Cochez, Y.; Martin, R. H.; Jespers, J. Isr. J. Chem. 1976, 15, 29. (j) Jutz, C.; Loebering, H.-G. Angew. Chem. 1975, 87, 415. (k) Martin, R. H. Chimia 1975, 29, 137. (l) Martin, R. H.; Cosyn, J. P. Synth. Commun. 1971, 1, 257.
38. For monophosphine, see: Terfort, A.; Gorls, H.; Brunner, H. Synthesis 1997, 79.
39. For bisphosphine, see refs 3a and 5 and the following: (a) Reetz, M. T.; Sostmann, S. J. Organomet. Chem. 2000, 603, 105. (b) Reetz, M. T.; Beuttenmuller, E. W.; Goddard, R. Tetrahedron Lett. 1997, 38, 3211.
40. For bisphosphine, see refs 3a and 5 and the following: (a) Reetz, M. T.; Sostmann, S. J. Organomet. Chem. 2000, 603, 105. (b) Reetz, M. T.; Beuttenmuller, E. W.; Goddard, R. Tetrahedron Lett. 1997, 38, 3211.
41. For amine, see: op den Brouw, P. M.; Laarhoven, W. H. Recl. Trav. Chim. Pays-Bas 1978, 97, 265.
42. For electrophilic substitution of parent hexahelicene, see ref 7.
43. Most of the functionalized helicenes mentioned in refs 3-7 were prepared from substituted stilbene-type precursors via impractical UV light-mediated photodehydrocyclization or, in the case of hydroxy derivatives, by benzoquinone cycloaddition to (bis)vinyl aromatics. Although the latter approach published by Katz is quite general in regard to the helicene skeleton, a substitution portfolio is very limited.
44. (a) Teplý, F.; Stará, I. G.; Starý, I.; Kollárovič, A.; Šaman, D.; Rulíšek, L.; Fiedler, P. J. Am. Chem. Soc. 2002, 124, 9175.
45. (b) Stará, I. G.; Starý, I.; Kollárovič, A.; Teply, F.; Vyskočil, Š.; Šaman, D. Tetrahedron Lett. 1999, 40, 1993.
46. Hoye, T. R.; Mi, L. J. Org. Chem. 1997, 62, 8596.
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52. To the best of our knowledge, this is the first example of enantioselective transition metal catalysis applied to the synthesis of substituted helicenes. Enantioselectivity achieved is not sufficient for the practical synthesis of nonracemic 12 and further search for a more effective chiral ligand is under way.
53. For review, see: Fu, P. P.; Harvey, R. G. Chem. Rev. 1978, 78, 317.
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59. Lindow, D. F.; Harvey, R. G. J. Am. Chem. Soc. 1971, 93, 3786.
60. 3-Methoxyhexahelicene 14 can be resolved into enantiomers on an inexpensive triacetylcellulose column. Unfortunately, its solubility in ethanol is too poor for the preparative HPLC separation.
61. 3-Hexahelicenol 15 was converted to the corresponding non-racemic camphor sulfonate, menthyl carbonate, and camphanate. No separation of diastereomers was observed in TLC (silica gel) or HPLC (Whelk O1) analyses.
62. Dolle, R. E.; Schmidt, S. J.; Kruse, L. I. J. Chem. Soc., Chem. Commun. 1987, 904.
63. For reviews, see: (a) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, Germany, 2000.
64. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
65. (c) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
66. (d) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
67. Wolfe, J. P.; Åhman, J.; Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6367.
68. Vyskočil, Š. Private communication.
69. Cossu, S.; De Lucchi, O.; Fabbri, D.; Valle, G.; Painter, G. F.; Smith, R. A. J. Tetrahedron 1997, 53, 6073.
70. 1H NMR and IR provided complex spectra due to the partial formation of diastereomeric disulfides.