Effect of the Michael Acceptor in the Asymmetric Intramolecular Stetter Reaction

Synlett

Volumn , Issue 12, 2003, Pages 1934-1936

  Kerr, Mark S ^a   Rovis, Tomislav ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

Catalytic asymmetric Stetter; Michael acceptors; Nucleophilic carbenes; Umpolung chemistry

Indexed keywords

CARBENE; SODIUM CHLORIDE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL BOND; CHIRALITY; ELECTRON; EVALUATION; MICHAEL ADDITION;

EID: 0142059744     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41458     Document Type: Article

References (20)

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7. The mechanistically related asymmetric benzoin reaction has received far more attention, see: (a) Sheehan, J. C.; Hunneman, D. H. J. Am. Chem. Soc. 1966, 88, 3666. (b) Sheehan, J. C.; Hara, T. J. Org. Chem. 1974, 39, 1196. (c) Martí, J.; Castells, J.; López-Calahorra, F. Tetrahedron Lett. 1993, 34, 521. (d) Yamashita, K.; Sasaki, S.-i.; Osaki, T.; Nango, M.; Tsuda, K. Tetrahedron Lett. 1995, 36, 4817. (e) Enders, D.; Breuer, K.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217. (f) Knight, R. L.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3611. (g) Gerhard, A. U.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3615. (h) Dvorak, C. A.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 2925. (i) Knight, R. L.; Leeper, F. J. J. Chem. Soc., Perkin Trans, 1 1998, 1891. (j) Enders, D.; Kallfass, U. Angew. Chem. Int. Ed. 2002, 41, 1743.
8. The mechanistically related asymmetric benzoin reaction has received far more attention, see: (a) Sheehan, J. C.; Hunneman, D. H. J. Am. Chem. Soc. 1966, 88, 3666. (b) Sheehan, J. C.; Hara, T. J. Org. Chem. 1974, 39, 1196. (c) Martí, J.; Castells, J.; López-Calahorra, F. Tetrahedron Lett. 1993, 34, 521. (d) Yamashita, K.; Sasaki, S.-i.; Osaki, T.; Nango, M.; Tsuda, K. Tetrahedron Lett. 1995, 36, 4817. (e) Enders, D.; Breuer, K.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217. (f) Knight, R. L.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3611. (g) Gerhard, A. U.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3615. (h) Dvorak, C. A.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 2925. (i) Knight, R. L.; Leeper, F. J. J. Chem. Soc., Perkin Trans, 1 1998, 1891. (j) Enders, D.; Kallfass, U. Angew. Chem. Int. Ed. 2002, 41, 1743.
9. The mechanistically related asymmetric benzoin reaction has received far more attention, see: (a) Sheehan, J. C.; Hunneman, D. H. J. Am. Chem. Soc. 1966, 88, 3666. (b) Sheehan, J. C.; Hara, T. J. Org. Chem. 1974, 39, 1196. (c) Martí, J.; Castells, J.; López-Calahorra, F. Tetrahedron Lett. 1993, 34, 521. (d) Yamashita, K.; Sasaki, S.-i.; Osaki, T.; Nango, M.; Tsuda, K. Tetrahedron Lett. 1995, 36, 4817. (e) Enders, D.; Breuer, K.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217. (f) Knight, R. L.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3611. (g) Gerhard, A. U.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3615. (h) Dvorak, C. A.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 2925. (i) Knight, R. L.; Leeper, F. J. J. Chem. Soc., Perkin Trans, 1 1998, 1891. (j) Enders, D.; Kallfass, U. Angew. Chem. Int. Ed. 2002, 41, 1743.
10. The mechanistically related asymmetric benzoin reaction has received far more attention, see: (a) Sheehan, J. C.; Hunneman, D. H. J. Am. Chem. Soc. 1966, 88, 3666. (b) Sheehan, J. C.; Hara, T. J. Org. Chem. 1974, 39, 1196. (c) Martí, J.; Castells, J.; López-Calahorra, F. Tetrahedron Lett. 1993, 34, 521. (d) Yamashita, K.; Sasaki, S.-i.; Osaki, T.; Nango, M.; Tsuda, K. Tetrahedron Lett. 1995, 36, 4817. (e) Enders, D.; Breuer, K.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217. (f) Knight, R. L.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3611. (g) Gerhard, A. U.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3615. (h) Dvorak, C. A.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 2925. (i) Knight, R. L.; Leeper, F. J. J. Chem. Soc., Perkin Trans, 1 1998, 1891. (j) Enders, D.; Kallfass, U. Angew. Chem. Int. Ed. 2002, 41, 1743.
11. The mechanistically related asymmetric benzoin reaction has received far more attention, see: (a) Sheehan, J. C.; Hunneman, D. H. J. Am. Chem. Soc. 1966, 88, 3666. (b) Sheehan, J. C.; Hara, T. J. Org. Chem. 1974, 39, 1196. (c) Martí, J.; Castells, J.; López-Calahorra, F. Tetrahedron Lett. 1993, 34, 521. (d) Yamashita, K.; Sasaki, S.-i.; Osaki, T.; Nango, M.; Tsuda, K. Tetrahedron Lett. 1995, 36, 4817. (e) Enders, D.; Breuer, K.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217. (f) Knight, R. L.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3611. (g) Gerhard, A. U.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3615. (h) Dvorak, C. A.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 2925. (i) Knight, R. L.; Leeper, F. J. J. Chem. Soc., Perkin Trans, 1 1998, 1891. (j) Enders, D.; Kallfass, U. Angew. Chem. Int. Ed. 2002, 41, 1743.
12. The mechanistically related asymmetric benzoin reaction has received far more attention, see: (a) Sheehan, J. C.; Hunneman, D. H. J. Am. Chem. Soc. 1966, 88, 3666. (b) Sheehan, J. C.; Hara, T. J. Org. Chem. 1974, 39, 1196. (c) Martí, J.; Castells, J.; López-Calahorra, F. Tetrahedron Lett. 1993, 34, 521. (d) Yamashita, K.; Sasaki, S.-i.; Osaki, T.; Nango, M.; Tsuda, K. Tetrahedron Lett. 1995, 36, 4817. (e) Enders, D.; Breuer, K.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217. (f) Knight, R. L.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3611. (g) Gerhard, A. U.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3615. (h) Dvorak, C. A.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 2925. (i) Knight, R. L.; Leeper, F. J. J. Chem. Soc., Perkin Trans, 1 1998, 1891. (j) Enders, D.; Kallfass, U. Angew. Chem. Int. Ed. 2002, 41, 1743.
13. The mechanistically related asymmetric benzoin reaction has received far more attention, see: (a) Sheehan, J. C.; Hunneman, D. H. J. Am. Chem. Soc. 1966, 88, 3666. (b) Sheehan, J. C.; Hara, T. J. Org. Chem. 1974, 39, 1196. (c) Martí, J.; Castells, J.; López-Calahorra, F. Tetrahedron Lett. 1993, 34, 521. (d) Yamashita, K.; Sasaki, S.-i.; Osaki, T.; Nango, M.; Tsuda, K. Tetrahedron Lett. 1995, 36, 4817. (e) Enders, D.; Breuer, K.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217. (f) Knight, R. L.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3611. (g) Gerhard, A. U.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3615. (h) Dvorak, C. A.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 2925. (i) Knight, R. L.; Leeper, F. J. J. Chem. Soc., Perkin Trans, 1 1998, 1891. (j) Enders, D.; Kallfass, U. Angew. Chem. Int. Ed. 2002, 41, 1743.
14. The mechanistically related asymmetric benzoin reaction has received far more attention, see: (a) Sheehan, J. C.; Hunneman, D. H. J. Am. Chem. Soc. 1966, 88, 3666. (b) Sheehan, J. C.; Hara, T. J. Org. Chem. 1974, 39, 1196. (c) Martí, J.; Castells, J.; López-Calahorra, F. Tetrahedron Lett. 1993, 34, 521. (d) Yamashita, K.; Sasaki, S.-i.; Osaki, T.; Nango, M.; Tsuda, K. Tetrahedron Lett. 1995, 36, 4817. (e) Enders, D.; Breuer, K.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217. (f) Knight, R. L.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3611. (g) Gerhard, A. U.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3615. (h) Dvorak, C. A.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 2925. (i) Knight, R. L.; Leeper, F. J. J. Chem. Soc., Perkin Trans, 1 1998, 1891. (j) Enders, D.; Kallfass, U. Angew. Chem. Int. Ed. 2002, 41, 1743.
15. The mechanistically related asymmetric benzoin reaction has received far more attention, see: (a) Sheehan, J. C.; Hunneman, D. H. J. Am. Chem. Soc. 1966, 88, 3666. (b) Sheehan, J. C.; Hara, T. J. Org. Chem. 1974, 39, 1196. (c) Martí, J.; Castells, J.; López-Calahorra, F. Tetrahedron Lett. 1993, 34, 521. (d) Yamashita, K.; Sasaki, S.-i.; Osaki, T.; Nango, M.; Tsuda, K. Tetrahedron Lett. 1995, 36, 4817. (e) Enders, D.; Breuer, K.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217. (f) Knight, R. L.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3611. (g) Gerhard, A. U.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3615. (h) Dvorak, C. A.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 2925. (i) Knight, R. L.; Leeper, F. J. J. Chem. Soc., Perkin Trans, 1 1998, 1891. (j) Enders, D.; Kallfass, U. Angew. Chem. Int. Ed. 2002, 41, 1743.
16. The mechanistically related asymmetric benzoin reaction has received far more attention, see: (a) Sheehan, J. C.; Hunneman, D. H. J. Am. Chem. Soc. 1966, 88, 3666. (b) Sheehan, J. C.; Hara, T. J. Org. Chem. 1974, 39, 1196. (c) Martí, J.; Castells, J.; López-Calahorra, F. Tetrahedron Lett. 1993, 34, 521. (d) Yamashita, K.; Sasaki, S.-i.; Osaki, T.; Nango, M.; Tsuda, K. Tetrahedron Lett. 1995, 36, 4817. (e) Enders, D.; Breuer, K.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217. (f) Knight, R. L.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3611. (g) Gerhard, A. U.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3615. (h) Dvorak, C. A.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 2925. (i) Knight, R. L.; Leeper, F. J. J. Chem. Soc., Perkin Trans, 1 1998, 1891. (j) Enders, D.; Kallfass, U. Angew. Chem. Int. Ed. 2002, 41, 1743.
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