Rationalization of product selectivities in asymmetric Horner-Wadsworth- Emmons reactions by use of a new method for transition-state modeling

Journal of Organic Chemistry

Volumn 64, Issue 16, 1999, Pages 5845-5852

  Norrby, Per Ola ^a   Brandt, Peter ^a   Rein, Tobias ^b  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; ENERGY; MOLECULAR MODEL; QUANTUM CHEMISTRY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033529735     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990318d     Document Type: Article

References (75)

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2. For a review, see: (a) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369. See also: (b) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (c) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. / Recueil 1997, 1283. Recent examples: (e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077. (f) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1990, 37, 3735. (g) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753. (h) Gais, H.-J.; Schmiedl, G.; Ossenkamp, R. K. L. Liebigs Ann. / Recueil 1997, 2419. (i) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979. (j) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375. (k) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (l) Kreuder, R., Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035. (m) Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. 1998, 110, 525; Angew. Chem., Int. Ed. Engl. 1998, 37, 515. (n) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem. 1998, 110, 2526; Angew. Chem., Int. Ed. Engl. 1998, 37, 2354. (o) Vaulont, I.; Gais, H.-J.; Reuter, N.; Schmitz, E.; Ossenkamp, R. K. L. Eur. J. Org. Chem. 1998, 63, 805. (p) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (q) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
3. For a review, see: (a) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369. See also: (b) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (c) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. / Recueil 1997, 1283. Recent examples: (e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077. (f) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1990, 37, 3735. (g) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753. (h) Gais, H.-J.; Schmiedl, G.; Ossenkamp, R. K. L. Liebigs Ann. / Recueil 1997, 2419. (i) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979. (j) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375. (k) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (l) Kreuder, R., Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035. (m) Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. 1998, 110, 525; Angew. Chem., Int. Ed. Engl. 1998, 37, 515. (n) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem. 1998, 110, 2526; Angew. Chem., Int. Ed. Engl. 1998, 37, 2354. (o) Vaulont, I.; Gais, H.-J.; Reuter, N.; Schmitz, E.; Ossenkamp, R. K. L. Eur. J. Org. Chem. 1998, 63, 805. (p) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (q) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
4. For a review, see: (a) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369. See also: (b) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (c) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. / Recueil 1997, 1283. Recent examples: (e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077. (f) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1990, 37, 3735. (g) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753. (h) Gais, H.-J.; Schmiedl, G.; Ossenkamp, R. K. L. Liebigs Ann. / Recueil 1997, 2419. (i) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979. (j) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375. (k) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (l) Kreuder, R., Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035. (m) Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. 1998, 110, 525; Angew. Chem., Int. Ed. Engl. 1998, 37, 515. (n) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem. 1998, 110, 2526; Angew. Chem., Int. Ed. Engl. 1998, 37, 2354. (o) Vaulont, I.; Gais, H.-J.; Reuter, N.; Schmitz, E.; Ossenkamp, R. K. L. Eur. J. Org. Chem. 1998, 63, 805. (p) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (q) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
5. For a review, see: (a) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369. See also: (b) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (c) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. / Recueil 1997, 1283. Recent examples: (e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077. (f) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1990, 37, 3735. (g) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753. (h) Gais, H.-J.; Schmiedl, G.; Ossenkamp, R. K. L. Liebigs Ann. / Recueil 1997, 2419. (i) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979. (j) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375. (k) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (l) Kreuder, R., Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035. (m) Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. 1998, 110, 525; Angew. Chem., Int. Ed. Engl. 1998, 37, 515. (n) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem. 1998, 110, 2526; Angew. Chem., Int. Ed. Engl. 1998, 37, 2354. (o) Vaulont, I.; Gais, H.-J.; Reuter, N.; Schmitz, E.; Ossenkamp, R. K. L. Eur. J. Org. Chem. 1998, 63, 805. (p) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (q) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
6. For a review, see: (a) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369. See also: (b) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (c) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. / Recueil 1997, 1283. Recent examples: (e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077. (f) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1990, 37, 3735. (g) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753. (h) Gais, H.-J.; Schmiedl, G.; Ossenkamp, R. K. L. Liebigs Ann. / Recueil 1997, 2419. (i) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979. (j) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375. (k) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (l) Kreuder, R., Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035. (m) Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. 1998, 110, 525; Angew. Chem., Int. Ed. Engl. 1998, 37, 515. (n) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem. 1998, 110, 2526; Angew. Chem., Int. Ed. Engl. 1998, 37, 2354. (o) Vaulont, I.; Gais, H.-J.; Reuter, N.; Schmitz, E.; Ossenkamp, R. K. L. Eur. J. Org. Chem. 1998, 63, 805. (p) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (q) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
7. For a review, see: (a) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369. See also: (b) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (c) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. / Recueil 1997, 1283. Recent examples: (e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077. (f) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1990, 37, 3735. (g) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753. (h) Gais, H.-J.; Schmiedl, G.; Ossenkamp, R. K. L. Liebigs Ann. / Recueil 1997, 2419. (i) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979. (j) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375. (k) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (l) Kreuder, R., Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035. (m) Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. 1998, 110, 525; Angew. Chem., Int. Ed. Engl. 1998, 37, 515. (n) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem. 1998, 110, 2526; Angew. Chem., Int. Ed. Engl. 1998, 37, 2354. (o) Vaulont, I.; Gais, H.-J.; Reuter, N.; Schmitz, E.; Ossenkamp, R. K. L. Eur. J. Org. Chem. 1998, 63, 805. (p) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (q) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
8. For a review, see: (a) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369. See also: (b) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (c) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. / Recueil 1997, 1283. Recent examples: (e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077. (f) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1990, 37, 3735. (g) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753. (h) Gais, H.-J.; Schmiedl, G.; Ossenkamp, R. K. L. Liebigs Ann. / Recueil 1997, 2419. (i) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979. (j) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375. (k) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (l) Kreuder, R., Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035. (m) Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. 1998, 110, 525; Angew. Chem., Int. Ed. Engl. 1998, 37, 515. (n) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem. 1998, 110, 2526; Angew. Chem., Int. Ed. Engl. 1998, 37, 2354. (o) Vaulont, I.; Gais, H.-J.; Reuter, N.; Schmitz, E.; Ossenkamp, R. K. L. Eur. J. Org. Chem. 1998, 63, 805. (p) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (q) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
9. For a review, see: (a) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369. See also: (b) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (c) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. / Recueil 1997, 1283. Recent examples: (e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077. (f) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1990, 37, 3735. (g) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753. (h) Gais, H.-J.; Schmiedl, G.; Ossenkamp, R. K. L. Liebigs Ann. / Recueil 1997, 2419. (i) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979. (j) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375. (k) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (l) Kreuder, R., Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035. (m) Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. 1998, 110, 525; Angew. Chem., Int. Ed. Engl. 1998, 37, 515. (n) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem. 1998, 110, 2526; Angew. Chem., Int. Ed. Engl. 1998, 37, 2354. (o) Vaulont, I.; Gais, H.-J.; Reuter, N.; Schmitz, E.; Ossenkamp, R. K. L. Eur. J. Org. Chem. 1998, 63, 805. (p) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (q) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
10. For a review, see: (a) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369. See also: (b) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (c) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. / Recueil 1997, 1283. Recent examples: (e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077. (f) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1990, 37, 3735. (g) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753. (h) Gais, H.-J.; Schmiedl, G.; Ossenkamp, R. K. L. Liebigs Ann. / Recueil 1997, 2419. (i) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979. (j) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375. (k) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (l) Kreuder, R., Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035. (m) Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. 1998, 110, 525; Angew. Chem., Int. Ed. Engl. 1998, 37, 515. (n) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem. 1998, 110, 2526; Angew. Chem., Int. Ed. Engl. 1998, 37, 2354. (o) Vaulont, I.; Gais, H.-J.; Reuter, N.; Schmitz, E.; Ossenkamp, R. K. L. Eur. J. Org. Chem. 1998, 63, 805. (p) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (q) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
11. For a review, see: (a) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369. See also: (b) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (c) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. / Recueil 1997, 1283. Recent examples: (e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077. (f) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1990, 37, 3735. (g) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753. (h) Gais, H.-J.; Schmiedl, G.; Ossenkamp, R. K. L. Liebigs Ann. / Recueil 1997, 2419. (i) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979. (j) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375. (k) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (l) Kreuder, R., Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035. (m) Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. 1998, 110, 525; Angew. Chem., Int. Ed. Engl. 1998, 37, 515. (n) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem. 1998, 110, 2526; Angew. Chem., Int. Ed. Engl. 1998, 37, 2354. (o) Vaulont, I.; Gais, H.-J.; Reuter, N.; Schmitz, E.; Ossenkamp, R. K. L. Eur. J. Org. Chem. 1998, 63, 805. (p) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (q) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
12. For a review, see: (a) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369. See also: (b) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (c) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. / Recueil 1997, 1283. Recent examples: (e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077. (f) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1990, 37, 3735. (g) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753. (h) Gais, H.-J.; Schmiedl, G.; Ossenkamp, R. K. L. Liebigs Ann. / Recueil 1997, 2419. (i) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979. (j) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375. (k) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (l) Kreuder, R., Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035. (m) Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. 1998, 110, 525; Angew. Chem., Int. Ed. Engl. 1998, 37, 515. (n) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem. 1998, 110, 2526; Angew. Chem., Int. Ed. Engl. 1998, 37, 2354. (o) Vaulont, I.; Gais, H.-J.; Reuter, N.; Schmitz, E.; Ossenkamp, R. K. L. Eur. J. Org. Chem. 1998, 63, 805. (p) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (q) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
13. For a review, see: (a) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369. See also: (b) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (c) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. / Recueil 1997, 1283. Recent examples: (e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077. (f) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1990, 37, 3735. (g) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753. (h) Gais, H.-J.; Schmiedl, G.; Ossenkamp, R. K. L. Liebigs Ann. / Recueil 1997, 2419. (i) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979. (j) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375. (k) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (l) Kreuder, R., Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035. (m) Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. 1998, 110, 525; Angew. Chem., Int. Ed. Engl. 1998, 37, 515. (n) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem. 1998, 110, 2526; Angew. Chem., Int. Ed. Engl. 1998, 37, 2354. (o) Vaulont, I.; Gais, H.-J.; Reuter, N.; Schmitz, E.; Ossenkamp, R. K. L. Eur. J. Org. Chem. 1998, 63, 805. (p) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (q) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
14. For a review, see: (a) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369. See also: (b) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (c) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. / Recueil 1997, 1283. Recent examples: (e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077. (f) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1990, 37, 3735. (g) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753. (h) Gais, H.-J.; Schmiedl, G.; Ossenkamp, R. K. L. Liebigs Ann. / Recueil 1997, 2419. (i) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979. (j) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375. (k) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (l) Kreuder, R., Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035. (m) Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. 1998, 110, 525; Angew. Chem., Int. Ed. Engl. 1998, 37, 515. (n) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem. 1998, 110, 2526; Angew. Chem., Int. Ed. Engl. 1998, 37, 2354. (o) Vaulont, I.; Gais, H.-J.; Reuter, N.; Schmitz, E.; Ossenkamp, R. K. L. Eur. J. Org. Chem. 1998, 63, 805. (p) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (q) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
15. For a review, see: (a) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369. See also: (b) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (c) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. / Recueil 1997, 1283. Recent examples: (e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077. (f) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1990, 37, 3735. (g) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753. (h) Gais, H.-J.; Schmiedl, G.; Ossenkamp, R. K. L. Liebigs Ann. / Recueil 1997, 2419. (i) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979. (j) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375. (k) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (l) Kreuder, R., Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035. (m) Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. 1998, 110, 525; Angew. Chem., Int. Ed. Engl. 1998, 37, 515. (n) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem. 1998, 110, 2526; Angew. Chem., Int. Ed. Engl. 1998, 37, 2354. (o) Vaulont, I.; Gais, H.-J.; Reuter, N.; Schmitz, E.; Ossenkamp, R. K. L. Eur. J. Org. Chem. 1998, 63, 805. (p) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (q) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
16. For a review, see: (a) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369. See also: (b) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (c) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. / Recueil 1997, 1283. Recent examples: (e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077. (f) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1990, 37, 3735. (g) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753. (h) Gais, H.-J.; Schmiedl, G.; Ossenkamp, R. K. L. Liebigs Ann. / Recueil 1997, 2419. (i) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979. (j) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375. (k) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (l) Kreuder, R., Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035. (m) Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. 1998, 110, 525; Angew. Chem., Int. Ed. Engl. 1998, 37, 515. (n) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem. 1998, 110, 2526; Angew. Chem., Int. Ed. Engl. 1998, 37, 2354. (o) Vaulont, I.; Gais, H.-J.; Reuter, N.; Schmitz, E.; Ossenkamp, R. K. L. Eur. J. Org. Chem. 1998, 63, 805. (p) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (q) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
17. For a review, see: (a) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369. See also: (b) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (c) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. / Recueil 1997, 1283. Recent examples: (e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077. (f) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1990, 37, 3735. (g) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753. (h) Gais, H.-J.; Schmiedl, G.; Ossenkamp, R. K. L. Liebigs Ann. / Recueil 1997, 2419. (i) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979. (j) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375. (k) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (l) Kreuder, R., Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035. (m) Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. 1998, 110, 525; Angew. Chem., Int. Ed. Engl. 1998, 37, 515. (n) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem. 1998, 110, 2526; Angew. Chem., Int. Ed. Engl. 1998, 37, 2354. (o) Vaulont, I.; Gais, H.-J.; Reuter, N.; Schmitz, E.; Ossenkamp, R. K. L. Eur. J. Org. Chem. 1998, 63, 805. (p) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (q) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
18. For a review, see: (a) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369. See also: (b) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (c) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. / Recueil 1997, 1283. Recent examples: (e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077. (f) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1990, 37, 3735. (g) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753. (h) Gais, H.-J.; Schmiedl, G.; Ossenkamp, R. K. L. Liebigs Ann. / Recueil 1997, 2419. (i) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979. (j) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375. (k) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (l) Kreuder, R., Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035. (m) Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. 1998, 110, 525; Angew. Chem., Int. Ed. Engl. 1998, 37, 515. (n) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem. 1998, 110, 2526; Angew. Chem., Int. Ed. Engl. 1998, 37, 2354. (o) Vaulont, I.; Gais, H.-J.; Reuter, N.; Schmitz, E.; Ossenkamp, R. K. L. Eur. J. Org. Chem. 1998, 63, 805. (p) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (q) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
19. For a review, see: (a) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369. See also: (b) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (c) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. (d) Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. / Recueil 1997, 1283. Recent examples: (e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077. (f) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1990, 37, 3735. (g) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753. (h) Gais, H.-J.; Schmiedl, G.; Ossenkamp, R. K. L. Liebigs Ann. / Recueil 1997, 2419. (i) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979. (j) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375. (k) Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943. (l) Kreuder, R., Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035. (m) Mizuno, M.; Fujii, K.; Tomioka, K. Angew. Chem. 1998, 110, 525; Angew. Chem., Int. Ed. Engl. 1998, 37, 515. (n) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem. 1998, 110, 2526; Angew. Chem., Int. Ed. Engl. 1998, 37, 2354. (o) Vaulont, I.; Gais, H.-J.; Reuter, N.; Schmitz, E.; Ossenkamp, R. K. L. Eur. J. Org. Chem. 1998, 63, 805. (p) Tullis, J. S.; Vares, L.; Kann, N.; Norrby, P.-O.; Rein, T. J. Org. Chem. 1998, 63, 8284. (q) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
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34. For a review, see: (a) Eksterowicz, J. E.; Houk, K. N. Chem. Rev. 1993, 93, 2439. For some examples, see: (b) Wu, Y.-D.; Wang, Y.; Houk, K. N. J. Org. Chem. 1992, 57, 1362. (c) de Pascual-Teresa, B.; Gonzalez, J.; Asensio, A.; Houk, K. N. J. Am. Chem. Soc. 1995, 117, 4347. (d) Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron: Asymmetry 1995, 6, 2613.
35. For a review, see: (a) Eksterowicz, J. E.; Houk, K. N. Chem. Rev. 1993, 93, 2439. For some examples, see: (b) Wu, Y.-D.; Wang, Y.; Houk, K. N. J. Org. Chem. 1992, 57, 1362. (c) de Pascual-Teresa, B.; Gonzalez, J.; Asensio, A.; Houk, K. N. J. Am. Chem. Soc. 1995, 117, 4347. (d) Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron: Asymmetry 1995, 6, 2613.
36. For a review, see: (a) Eksterowicz, J. E.; Houk, K. N. Chem. Rev. 1993, 93, 2439. For some examples, see: (b) Wu, Y.-D.; Wang, Y.; Houk, K. N. J. Org. Chem. 1992, 57, 1362. (c) de Pascual-Teresa, B.; Gonzalez, J.; Asensio, A.; Houk, K. N. J. Am. Chem. Soc. 1995, 117, 4347. (d) Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron: Asymmetry 1995, 6, 2613.
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