Enantioselective construction of carbobicyclic scaffolds

Journal of the American Chemical Society

Volumn 126, Issue 43, 2004, Pages 13900-13901

  Taber, Douglass F ^a   He, Yigang ^a   Xu, Ming ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; CYCLOHEXENE DERIVATIVE; CYCLOPENTENE DERIVATIVE; EPOXIDE; LEWIS ACID;

ALKYLATION; ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOSELECTIVITY; EPOXIDATION; GRIGNARD REACTION; SUBSTITUTION REACTION;

BICYCLO COMPOUNDS; CYCLIZATION; EPOXY COMPOUNDS; STEREOISOMERISM;

EID: 7444231089     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045849k     Document Type: Article

References (34)

1. The enyne corresponding to epoxide 1a was prepared by the addition of lithiated phenylacetylene to cycloheptanone followed by dehydration: Davies, M. T.; Dobson, D. F.; Hayman, D. F.; Jackman, G. B.; Lester, M. G.; Petrow, V.; Stephenson, O.; Webb, A. A. Tetrahedron 1962, 18, 751.
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4. For the only reports to date of the opening of an alkynyl-activated trisubstituted epoxide at the more substituted carbon atom to establish a quaternary center, see: (a) Perveev, F. Y.; Kudryashova, N. I. Zh. Obshch. Khim. 1953, 23, 348. (b) Aurrecoechea, J. M.; Alonso, E.; Solay, M. Tetrahedron 1998, 54, 3833 (only partially selective).
5. For the only reports to date of the opening of an alkynyl-activated trisubstituted epoxide at the more substituted carbon atom to establish a quaternary center, see: (a) Perveev, F. Y.; Kudryashova, N. I. Zh. Obshch. Khim. 1953, 23, 348. (b) Aurrecoechea, J. M.; Alonso, E.; Solay, M. Tetrahedron 1998, 54, 3833 (only partially selective).
6. For the opening of phenyl-activated trisubstituted epoxides at the more substituted carbon to establish a quaternary center, see: (c) Gerteisen, T. J.; Kleinfelter, D. C. J. Org. Chem. 1971, 36, 3255. (d) Krause, N.; Seebach, D. Chem. Ber. 1988, 121, 1315. (e) Kauffmann, T.; Neiteler, C.; Robbe, S. Chem. Ber. 1992, 125, 2409. (f) Jansen, J.; Knopp, M.; Amberg, W.; Bernard, H.; Koser, S.; Müller, S.; Münster, I.; Pfeiffer, T.; Riechers, H. Org. Process Res. Dev. 2001, 5, 16.
7. For the opening of phenyl-activated trisubstituted epoxides at the more substituted carbon to establish a quaternary center, see: (c) Gerteisen, T. J.; Kleinfelter, D. C. J. Org. Chem. 1971, 36, 3255. (d) Krause, N.; Seebach, D. Chem. Ber. 1988, 121, 1315. (e) Kauffmann, T.; Neiteler, C.; Robbe, S. Chem. Ber. 1992, 125, 2409. (f) Jansen, J.; Knopp, M.; Amberg, W.; Bernard, H.; Koser, S.; Müller, S.; Münster, I.; Pfeiffer, T.; Riechers, H. Org. Process Res. Dev. 2001, 5, 16.
8. For the opening of phenyl-activated trisubstituted epoxides at the more substituted carbon to establish a quaternary center, see: (c) Gerteisen, T. J.; Kleinfelter, D. C. J. Org. Chem. 1971, 36, 3255. (d) Krause, N.; Seebach, D. Chem. Ber. 1988, 121, 1315. (e) Kauffmann, T.; Neiteler, C.; Robbe, S. Chem. Ber. 1992, 125, 2409. (f) Jansen, J.; Knopp, M.; Amberg, W.; Bernard, H.; Koser, S.; Müller, S.; Münster, I.; Pfeiffer, T.; Riechers, H. Org. Process Res. Dev. 2001, 5, 16.
9. For the opening of phenyl-activated trisubstituted epoxides at the more substituted carbon to establish a quaternary center, see: (c) Gerteisen, T. J.; Kleinfelter, D. C. J. Org. Chem. 1971, 36, 3255. (d) Krause, N.; Seebach, D. Chem. Ber. 1988, 121, 1315. (e) Kauffmann, T.; Neiteler, C.; Robbe, S. Chem. Ber. 1992, 125, 2409. (f) Jansen, J.; Knopp, M.; Amberg, W.; Bernard, H.; Koser, S.; Müller, S.; Münster, I.; Pfeiffer, T.; Riechers, H. Org. Process Res. Dev. 2001, 5, 16.
10. For the opening of alkenyl-activated trisubstituted epoxides at the more substituted center to establish a quaternary center, see ref 3d and: (g) Ishibashi, N.; Miyazawa, M.; Miyashita, M. Tetrahedron Lett. 1998, 39, 3775.
11. For the opening of trisubstituted 2,3-epoxy alcohols or ethers at the more substituted carbon to establish a quaternary center, see: (h) Newbold, R. C.; Shih, T. L.; Mrozik, H.; Fisher, M. H. Tetrahedron Lett. 1993, 34, 3825. (i) Balasubramaniam, R. P.; Moss, D. K.; Wyatt, J. K.; Spence, T. D.; Gee, A.; Nantz, M. H. Tetrahedron 1997, 53, 7429. (j) Benedetti, F.; Berti, F.; Norbedo, S. Tetrahedron Lett. 1999, 40, 1041. (k) Zhao, H.; Pagenkopf, B. L. Chem. Commun. 2003, 2592. (l) Ohno, H.; Hiramatsu, K.; Tanaka, T. Tetrahedron Lett. 2004, 45, 75. For the opening of trialkyl-substituted epoxides at the more substituted carbon to establish a quaternary center, see ref 3k.
12. For the opening of trisubstituted 2,3-epoxy alcohols or ethers at the more substituted carbon to establish a quaternary center, see: (h) Newbold, R. C.; Shih, T. L.; Mrozik, H.; Fisher, M. H. Tetrahedron Lett. 1993, 34, 3825. (i) Balasubramaniam, R. P.; Moss, D. K.; Wyatt, J. K.; Spence, T. D.; Gee, A.; Nantz, M. H. Tetrahedron 1997, 53, 7429. (j) Benedetti, F.; Berti, F.; Norbedo, S. Tetrahedron Lett. 1999, 40, 1041. (k) Zhao, H.; Pagenkopf, B. L. Chem. Commun. 2003, 2592. (l) Ohno, H.; Hiramatsu, K.; Tanaka, T. Tetrahedron Lett. 2004, 45, 75. For the opening of trialkyl-substituted epoxides at the more substituted carbon to establish a quaternary center, see ref 3k.
13. For the opening of trisubstituted 2,3-epoxy alcohols or ethers at the more substituted carbon to establish a quaternary center, see: (h) Newbold, R. C.; Shih, T. L.; Mrozik, H.; Fisher, M. H. Tetrahedron Lett. 1993, 34, 3825. (i) Balasubramaniam, R. P.; Moss, D. K.; Wyatt, J. K.; Spence, T. D.; Gee, A.; Nantz, M. H. Tetrahedron 1997, 53, 7429. (j) Benedetti, F.; Berti, F.; Norbedo, S. Tetrahedron Lett. 1999, 40, 1041. (k) Zhao, H.; Pagenkopf, B. L. Chem. Commun. 2003, 2592. (l) Ohno, H.; Hiramatsu, K.; Tanaka, T. Tetrahedron Lett. 2004, 45, 75. For the opening of trialkyl-substituted epoxides at the more substituted carbon to establish a quaternary center, see ref 3k.
14. For the opening of trisubstituted 2,3-epoxy alcohols or ethers at the more substituted carbon to establish a quaternary center, see: (h) Newbold, R. C.; Shih, T. L.; Mrozik, H.; Fisher, M. H. Tetrahedron Lett. 1993, 34, 3825. (i) Balasubramaniam, R. P.; Moss, D. K.; Wyatt, J. K.; Spence, T. D.; Gee, A.; Nantz, M. H. Tetrahedron 1997, 53, 7429. (j) Benedetti, F.; Berti, F.; Norbedo, S. Tetrahedron Lett. 1999, 40, 1041. (k) Zhao, H.; Pagenkopf, B. L. Chem. Commun. 2003, 2592. (l) Ohno, H.; Hiramatsu, K.; Tanaka, T. Tetrahedron Lett. 2004, 45, 75. For the opening of trialkyl-substituted epoxides at the more substituted carbon to establish a quaternary center, see ref 3k.
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24. Conditions: Chiral HPLC, Chiralcel OD, 1% 2-propanol/hexane, 1 mL/ min, retention time of 33.5 min for the major enantiomer and 38.6 min for the minor enantiomer. Shi's group demonstrated that asymmetric epoxidation gave much higher ee with the six-membered alkynyl alkene (ref 2).
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