Catalytic asymmetric intramolecular aminopalladation: Improved palladium(II) catalysts

Journal of Organic Chemistry

Volumn 70, Issue 7, 2005, Pages 2859-2861

  Kirsch, Stefan F ^a   Overman, Larry E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; ORGANOMETALLICS; PALLADIUM; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CYCLIZATION; INTRAMOLECULAR AMINOPALLADATION; LIGANDS; SILVER SALTS;

CATALYSIS;

4 VINYLOXAZOLIDIN 2 ONE DERIVATIVE; CARBAMIC ACID DERIVATIVE; COBALT COMPLEX; LIGAND; OXAZOLINE DERIVATIVE; PALLADIUM; PALLADIUM COMPLEX; SILVER DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

AMINOPALLADATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; CYCLIZATION; SYNTHESIS;

EID: 17044433061     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo047763f     Document Type: Article

References (36)

1. For the first examples, see: (a) Hosokawa, T.; Miyagi, S.; Murahashi, D.-I.; Sonoda, A. J. Chem. Soc., Chem. Commun. 1978, 687-688. (b) Hosokawa, T.; Uno, T.; Inui, S.; Murahashi, S.-I. J. Am. Chem. Soc. 1981, 103, 2318-2323. (c) Hosokawa, T.; Murahashi, S.-I. Acc. Chem. Res. 1990, 23, 49-54.
2. For the first examples, see: (a) Hosokawa, T.; Miyagi, S.; Murahashi, D.-I.; Sonoda, A. J. Chem. Soc., Chem. Commun. 1978, 687-688. (b) Hosokawa, T.; Uno, T.; Inui, S.; Murahashi, S.-I. J. Am. Chem. Soc. 1981, 103, 2318-2323. (c) Hosokawa, T.; Murahashi, S.-I. Acc. Chem. Res. 1990, 23, 49-54.
3. For the first examples, see: (a) Hosokawa, T.; Miyagi, S.; Murahashi, D.-I.; Sonoda, A. J. Chem. Soc., Chem. Commun. 1978, 687-688. (b) Hosokawa, T.; Uno, T.; Inui, S.; Murahashi, S.-I. J. Am. Chem. Soc. 1981, 103, 2318-2323. (c) Hosokawa, T.; Murahashi, S.-I. Acc. Chem. Res. 1990, 23, 49-54.
4. Tsuji, J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century; Wiley: Chichester, England, 2004.
5. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
6. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
7. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
8. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
9. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
10. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
11. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
12. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
13. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
14. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
15. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
16. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
17. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
18. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
19. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
20. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
21. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
22. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
23. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
24. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
25. Allylic imidate rearrangements: (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456. (b) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065-1072. (d) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222. (e) Jiang, Y.; Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449-1450. (f) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435-2436. (g) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934. (h) Kang, J.; Hyung, K. Y.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509-9512. (i) Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418. Synthesis of heterocycles: (j) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063-5064. (k) Uozumi, Y.; Kyota, H.; Kato, K.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 1999, 64, 1620-1625. (l) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605. (m) Arai, M. A.; Kuraishi, M.; Arai, T.; Sasai, H. J. Am. Chem. Soc. 2001, 123, 2907-2908. (n) Tietze, L. F.; Sommer, K. M.; Zinngrebe, J.; Stecker, F. Angew. Chem., Int. Ed. 2005, 44, 257-259. Other reactions: (o) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648-2649. (p) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366-2368. (q) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. (r) El-Qisairi, A.; Hamed, O.; Henry, P. M. J. Org. Chem. 1998, 63, 2790-2791. (s) Mikami, K.; Hatano, M.; Terada, M. Chem. Lett. 1999, 55-56. (t) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 1999, 121, 6960-6961. (u) Stark, M. A.; Jones, G.; Richards, C. J. Organometallics 2000, 19, 1282-1291.
26. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13.
27. For a non-asymmetric variant of this reaction, see: Lei, A.; Liu, G.; Lu, X. J. Org. Chem. 2002, 67, 974-980.
28. (a) Anderson, C. E.; Kirsch, S. F.; Overman, L. E.; Richards, C. J.; Watson, M. P. Org. Synth., submitted for publication; available from the senior author upon request.
29. (b) Stevens, A. M.; Richards, C. J. Organometallics 1999, 18, 1346-1348.
30. 2 at room temperature with 2.5 equiv of AgOAc, followed by filtration through silica gel. (S)-COP-Cl is available currently from Aldrich Chemical Co. (64663-6); both (S)-and (R)-COP-OAc will be available commercially shortly.
31. (a) Kirsch, S. F.; Overman, L. E.; Watson, M. P. J. Org. Chem. 2004, 69, 8101-8104.
32. (b) Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003, 125, 12412-12413.
33. (c) Overman, L. E.; Owen, C. E.; Pavan, M. M.; Richards, C. J. Org. Lett. 2003, 5, 1809-1812.
34. Kirsch, S. F.; Overman, L. E. J. Am. Chem. Soc., in press.
35. 3CN, acetone and THF under identical conditions, catalyst 3 showed lower reactivity with enantioselectivities ≤60% ee.
36. The origin of this effect remains unclear.