Thiazolium-mediated multicomponent reactions: A facile synthesis of 3-aminofuran derivatives

Organic Letters

Volumn 7, Issue 7, 2005, Pages 1343-1345

  Ma, Cheng ^a   Yang, Yewei ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; ALDEHYDE; FURAN DERIVATIVE; SODIUM CHLORIDE; THIAZOLE DERIVATIVE;

ARTICLE; SYNTHESIS;

EID: 17544377678     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0501368     Document Type: Article

References (59)

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9. For the synthesis of furans from acyclic precursors, see: (a) Nair, V.; Vinod, A. U. Chem. Commun. 2000, 1019. (b) Jung, C.-K.; Wang, J.-C.; Krische M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Lee, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992. (d) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280. (e) Ma, S.-M.; Zhang, J.-L. J. Am. Chem. Soc. 2003, 125, 12386. (f) Yao, T.-L.; Zhang, X.-X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164. (g) Marshall, J. A.; Bennett, C. E. J. Org. Chem. 1994, 59, 6110. (h) Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 960. (i) Méndez-Andino, J.; Paquette, L. A. Org. Lett. 2000, 2, 4095.; (j) Liu, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (k) Redman, A. M.; Dumas, J.; Scoyy, W. J. Org. Lett. 2000, 2, 2061. (l) Nakamura, M.; Liang, C.; Nakamura, E. Org. Lett. 2004, 6, 2015.
10. For the synthesis of furans from acyclic precursors, see: (a) Nair, V.; Vinod, A. U. Chem. Commun. 2000, 1019. (b) Jung, C.-K.; Wang, J.-C.; Krische M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Lee, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992. (d) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280. (e) Ma, S.-M.; Zhang, J.-L. J. Am. Chem. Soc. 2003, 125, 12386. (f) Yao, T.-L.; Zhang, X.-X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164. (g) Marshall, J. A.; Bennett, C. E. J. Org. Chem. 1994, 59, 6110. (h) Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 960. (i) Méndez-Andino, J.; Paquette, L. A. Org. Lett. 2000, 2, 4095.; (j) Liu, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (k) Redman, A. M.; Dumas, J.; Scoyy, W. J. Org. Lett. 2000, 2, 2061. (l) Nakamura, M.; Liang, C.; Nakamura, E. Org. Lett. 2004, 6, 2015.
11. For the synthesis of furans from acyclic precursors, see: (a) Nair, V.; Vinod, A. U. Chem. Commun. 2000, 1019. (b) Jung, C.-K.; Wang, J.-C.; Krische M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Lee, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992. (d) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280. (e) Ma, S.-M.; Zhang, J.-L. J. Am. Chem. Soc. 2003, 125, 12386. (f) Yao, T.-L.; Zhang, X.-X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164. (g) Marshall, J. A.; Bennett, C. E. J. Org. Chem. 1994, 59, 6110. (h) Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 960. (i) Méndez-Andino, J.; Paquette, L. A. Org. Lett. 2000, 2, 4095.; (j) Liu, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (k) Redman, A. M.; Dumas, J.; Scoyy, W. J. Org. Lett. 2000, 2, 2061. (l) Nakamura, M.; Liang, C.; Nakamura, E. Org. Lett. 2004, 6, 2015.
12. For the synthesis of furans from acyclic precursors, see: (a) Nair, V.; Vinod, A. U. Chem. Commun. 2000, 1019. (b) Jung, C.-K.; Wang, J.-C.; Krische M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Lee, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992. (d) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280. (e) Ma, S.-M.; Zhang, J.-L. J. Am. Chem. Soc. 2003, 125, 12386. (f) Yao, T.-L.; Zhang, X.-X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164. (g) Marshall, J. A.; Bennett, C. E. J. Org. Chem. 1994, 59, 6110. (h) Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 960. (i) Méndez-Andino, J.; Paquette, L. A. Org. Lett. 2000, 2, 4095.; (j) Liu, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (k) Redman, A. M.; Dumas, J.; Scoyy, W. J. Org. Lett. 2000, 2, 2061. (l) Nakamura, M.; Liang, C.; Nakamura, E. Org. Lett. 2004, 6, 2015.
13. For the synthesis of furans from acyclic precursors, see: (a) Nair, V.; Vinod, A. U. Chem. Commun. 2000, 1019. (b) Jung, C.-K.; Wang, J.-C.; Krische M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Lee, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992. (d) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280. (e) Ma, S.-M.; Zhang, J.-L. J. Am. Chem. Soc. 2003, 125, 12386. (f) Yao, T.-L.; Zhang, X.-X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164. (g) Marshall, J. A.; Bennett, C. E. J. Org. Chem. 1994, 59, 6110. (h) Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 960. (i) Méndez-Andino, J.; Paquette, L. A. Org. Lett. 2000, 2, 4095.; (j) Liu, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (k) Redman, A. M.; Dumas, J.; Scoyy, W. J. Org. Lett. 2000, 2, 2061. (l) Nakamura, M.; Liang, C.; Nakamura, E. Org. Lett. 2004, 6, 2015.
14. For the synthesis of furans from acyclic precursors, see: (a) Nair, V.; Vinod, A. U. Chem. Commun. 2000, 1019. (b) Jung, C.-K.; Wang, J.-C.; Krische M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Lee, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992. (d) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280. (e) Ma, S.-M.; Zhang, J.-L. J. Am. Chem. Soc. 2003, 125, 12386. (f) Yao, T.-L.; Zhang, X.-X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164. (g) Marshall, J. A.; Bennett, C. E. J. Org. Chem. 1994, 59, 6110. (h) Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 960. (i) Méndez-Andino, J.; Paquette, L. A. Org. Lett. 2000, 2, 4095.; (j) Liu, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (k) Redman, A. M.; Dumas, J.; Scoyy, W. J. Org. Lett. 2000, 2, 2061. (l) Nakamura, M.; Liang, C.; Nakamura, E. Org. Lett. 2004, 6, 2015.
15. For the synthesis of furans from acyclic precursors, see: (a) Nair, V.; Vinod, A. U. Chem. Commun. 2000, 1019. (b) Jung, C.-K.; Wang, J.-C.; Krische M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Lee, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992. (d) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280. (e) Ma, S.-M.; Zhang, J.-L. J. Am. Chem. Soc. 2003, 125, 12386. (f) Yao, T.-L.; Zhang, X.-X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164. (g) Marshall, J. A.; Bennett, C. E. J. Org. Chem. 1994, 59, 6110. (h) Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 960. (i) Méndez-Andino, J.; Paquette, L. A. Org. Lett. 2000, 2, 4095.; (j) Liu, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (k) Redman, A. M.; Dumas, J.; Scoyy, W. J. Org. Lett. 2000, 2, 2061. (l) Nakamura, M.; Liang, C.; Nakamura, E. Org. Lett. 2004, 6, 2015.
16. For the synthesis of furans from acyclic precursors, see: (a) Nair, V.; Vinod, A. U. Chem. Commun. 2000, 1019. (b) Jung, C.-K.; Wang, J.-C.; Krische M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Lee, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992. (d) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280. (e) Ma, S.-M.; Zhang, J.-L. J. Am. Chem. Soc. 2003, 125, 12386. (f) Yao, T.-L.; Zhang, X.-X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164. (g) Marshall, J. A.; Bennett, C. E. J. Org. Chem. 1994, 59, 6110. (h) Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 960. (i) Méndez-Andino, J.; Paquette, L. A. Org. Lett. 2000, 2, 4095.; (j) Liu, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (k) Redman, A. M.; Dumas, J.; Scoyy, W. J. Org. Lett. 2000, 2, 2061. (l) Nakamura, M.; Liang, C.; Nakamura, E. Org. Lett. 2004, 6, 2015.
17. For the synthesis of furans from acyclic precursors, see: (a) Nair, V.; Vinod, A. U. Chem. Commun. 2000, 1019. (b) Jung, C.-K.; Wang, J.-C.; Krische M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Lee, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992. (d) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280. (e) Ma, S.-M.; Zhang, J.-L. J. Am. Chem. Soc. 2003, 125, 12386. (f) Yao, T.-L.; Zhang, X.-X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164. (g) Marshall, J. A.; Bennett, C. E. J. Org. Chem. 1994, 59, 6110. (h) Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 960. (i) Méndez-Andino, J.; Paquette, L. A. Org. Lett. 2000, 2, 4095.; (j) Liu, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (k) Redman, A. M.; Dumas, J.; Scoyy, W. J. Org. Lett. 2000, 2, 2061. (l) Nakamura, M.; Liang, C.; Nakamura, E. Org. Lett. 2004, 6, 2015.
18. For the synthesis of furans from acyclic precursors, see: (a) Nair, V.; Vinod, A. U. Chem. Commun. 2000, 1019. (b) Jung, C.-K.; Wang, J.-C.; Krische M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Lee, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992. (d) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280. (e) Ma, S.-M.; Zhang, J.-L. J. Am. Chem. Soc. 2003, 125, 12386. (f) Yao, T.-L.; Zhang, X.-X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164. (g) Marshall, J. A.; Bennett, C. E. J. Org. Chem. 1994, 59, 6110. (h) Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 960. (i) Méndez-Andino, J.; Paquette, L. A. Org. Lett. 2000, 2, 4095.; (j) Liu, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (k) Redman, A. M.; Dumas, J.; Scoyy, W. J. Org. Lett. 2000, 2, 2061. (l) Nakamura, M.; Liang, C.; Nakamura, E. Org. Lett. 2004, 6, 2015.
19. For the synthesis of furans from acyclic precursors, see: (a) Nair, V.; Vinod, A. U. Chem. Commun. 2000, 1019. (b) Jung, C.-K.; Wang, J.-C.; Krische M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Lee, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992. (d) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280. (e) Ma, S.-M.; Zhang, J.-L. J. Am. Chem. Soc. 2003, 125, 12386. (f) Yao, T.-L.; Zhang, X.-X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164. (g) Marshall, J. A.; Bennett, C. E. J. Org. Chem. 1994, 59, 6110. (h) Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 960. (i) Méndez-Andino, J.; Paquette, L. A. Org. Lett. 2000, 2, 4095.; (j) Liu, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (k) Redman, A. M.; Dumas, J.; Scoyy, W. J. Org. Lett. 2000, 2, 2061. (l) Nakamura, M.; Liang, C.; Nakamura, E. Org. Lett. 2004, 6, 2015.
20. For the synthesis of furans from acyclic precursors, see: (a) Nair, V.; Vinod, A. U. Chem. Commun. 2000, 1019. (b) Jung, C.-K.; Wang, J.-C.; Krische M. J. J. Am. Chem. Soc. 2004, 126, 4118. (c) Lee, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992. (d) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280. (e) Ma, S.-M.; Zhang, J.-L. J. Am. Chem. Soc. 2003, 125, 12386. (f) Yao, T.-L.; Zhang, X.-X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164. (g) Marshall, J. A.; Bennett, C. E. J. Org. Chem. 1994, 59, 6110. (h) Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 960. (i) Méndez-Andino, J.; Paquette, L. A. Org. Lett. 2000, 2, 4095.; (j) Liu, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (k) Redman, A. M.; Dumas, J.; Scoyy, W. J. Org. Lett. 2000, 2, 2061. (l) Nakamura, M.; Liang, C.; Nakamura, E. Org. Lett. 2004, 6, 2015.
21. For N-heterocyclic carbenes, see: (a) Wanzlick, H.-W.; Schikora, E. Angew. Chem. 1960, 72, 494. (b) Wanzlick, H.-W.; Schonherr, H.-J. Angew. Chem., Int. Ed. Engl. 1968, 7, 141. (c) Arduengo, A. J., III; Harlow, R. L.; Kline, M. K. J. Am. Chem. Soc. 1991, 113, 9704. (d) Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913. (e) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (f) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162. (g) Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem., Int. Ed. 2004, 43, 5130.
22. For N-heterocyclic carbenes, see: (a) Wanzlick, H.-W.; Schikora, E. Angew. Chem. 1960, 72, 494. (b) Wanzlick, H.-W.; Schonherr, H.-J. Angew. Chem., Int. Ed. Engl. 1968, 7, 141. (c) Arduengo, A. J., III; Harlow, R. L.; Kline, M. K. J. Am. Chem. Soc. 1991, 113, 9704. (d) Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913. (e) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (f) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162. (g) Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem., Int. Ed. 2004, 43, 5130.
23. For N-heterocyclic carbenes, see: (a) Wanzlick, H.-W.; Schikora, E. Angew. Chem. 1960, 72, 494. (b) Wanzlick, H.-W.; Schonherr, H.-J. Angew. Chem., Int. Ed. Engl. 1968, 7, 141. (c) Arduengo, A. J., III; Harlow, R. L.; Kline, M. K. J. Am. Chem. Soc. 1991, 113, 9704. (d) Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913. (e) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (f) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162. (g) Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem., Int. Ed. 2004, 43, 5130.
24. For N-heterocyclic carbenes, see: (a) Wanzlick, H.-W.; Schikora, E. Angew. Chem. 1960, 72, 494. (b) Wanzlick, H.-W.; Schonherr, H.-J. Angew. Chem., Int. Ed. Engl. 1968, 7, 141. (c) Arduengo, A. J., III; Harlow, R. L.; Kline, M. K. J. Am. Chem. Soc. 1991, 113, 9704. (d) Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913. (e) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (f) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162. (g) Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem., Int. Ed. 2004, 43, 5130.
25. For N-heterocyclic carbenes, see: (a) Wanzlick, H.-W.; Schikora, E. Angew. Chem. 1960, 72, 494. (b) Wanzlick, H.-W.; Schonherr, H.-J. Angew. Chem., Int. Ed. Engl. 1968, 7, 141. (c) Arduengo, A. J., III; Harlow, R. L.; Kline, M. K. J. Am. Chem. Soc. 1991, 113, 9704. (d) Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913. (e) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (f) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162. (g) Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem., Int. Ed. 2004, 43, 5130.
26. For N-heterocyclic carbenes, see: (a) Wanzlick, H.-W.; Schikora, E. Angew. Chem. 1960, 72, 494. (b) Wanzlick, H.-W.; Schonherr, H.-J. Angew. Chem., Int. Ed. Engl. 1968, 7, 141. (c) Arduengo, A. J., III; Harlow, R. L.; Kline, M. K. J. Am. Chem. Soc. 1991, 113, 9704. (d) Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913. (e) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (f) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162. (g) Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem., Int. Ed. 2004, 43, 5130.
27. For N-heterocyclic carbenes, see: (a) Wanzlick, H.-W.; Schikora, E. Angew. Chem. 1960, 72, 494. (b) Wanzlick, H.-W.; Schonherr, H.-J. Angew. Chem., Int. Ed. Engl. 1968, 7, 141. (c) Arduengo, A. J., III; Harlow, R. L.; Kline, M. K. J. Am. Chem. Soc. 1991, 113, 9704. (d) Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913. (e) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (f) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162. (g) Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem., Int. Ed. 2004, 43, 5130.
28. For selected reviews, see: (a) Cheng, Y.; Meth-Cohn, O. Chem. Rev. 2004, 104, 2507. (b) Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathen, J. S.; Balagopal, L. Acc. Chem. Res. 2003, 36, 899.
29. For selected reviews, see: (a) Cheng, Y.; Meth-Cohn, O. Chem. Rev. 2004, 104, 2507. (b) Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathen, J. S.; Balagopal, L. Acc. Chem. Res. 2003, 36, 899.
30. Nair, V.; Bindu, S.; Sreekumar, V.; Rath. N. P. Org. Lett. 2003, 5, 665.
31. The mechanism which is generally accepted for thiazolium-catalyzed reaction was proposed by Breslow, where thiazol-2-ylidene 2 was thought to act as the actual catalyst. An alternative mechanistic model based on the formation of carbene dimers was presented by Lemal et al. and extended by López Calahorra et al. in the 1980s. For the competing models, see: (a) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719. (b) Lemal, D. M.; Lovaid, R. A.; Kawano, K. I. J. Am. Chem. Soc. 1964, 86, 2518. (c) Castells, J.; López Calahorra, F.; Domingo, L. J. Org. Chem. 1988, 53, 4433.
32. The mechanism which is generally accepted for thiazolium-catalyzed reaction was proposed by Breslow, where thiazol-2-ylidene 2 was thought to act as the actual catalyst. An alternative mechanistic model based on the formation of carbene dimers was presented by Lemal et al. and extended by López Calahorra et al. in the 1980s. For the competing models, see: (a) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719. (b) Lemal, D. M.; Lovaid, R. A.; Kawano, K. I. J. Am. Chem. Soc. 1964, 86, 2518. (c) Castells, J.; López Calahorra, F.; Domingo, L. J. Org. Chem. 1988, 53, 4433.
33. The mechanism which is generally accepted for thiazolium-catalyzed reaction was proposed by Breslow, where thiazol-2-ylidene 2 was thought to act as the actual catalyst. An alternative mechanistic model based on the formation of carbene dimers was presented by Lemal et al. and extended by López Calahorra et al. in the 1980s. For the competing models, see: (a) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719. (b) Lemal, D. M.; Lovaid, R. A.; Kawano, K. I. J. Am. Chem. Soc. 1964, 86, 2518. (c) Castells, J.; López Calahorra, F.; Domingo, L. J. Org. Chem. 1988, 53, 4433.
34. For the ring opening of thiazoliun salts with nucleophiles, see: (a) Duclos J. M.; Haake, P. Biochemistry 1974, 13, 5358. (b) Hajós, Gy.; Messmer, A. J. J. Heterocycl. Chem. 1984, 21, 809. (c) Singh, H.; Lal, K. J. Chem. Soc., Perkin Trans. 1 1972, 1799. (d) Zoltewicz, J. A.; Uray, G. J. Org. Chem. 1980, 45, 2104.
35. For the ring opening of thiazoliun salts with nucleophiles, see: (a) Duclos J. M.; Haake, P. Biochemistry 1974, 13, 5358. (b) Hajós, Gy.; Messmer, A. J. J. Heterocycl. Chem. 1984, 21, 809. (c) Singh, H.; Lal, K. J. Chem. Soc., Perkin Trans. 1 1972, 1799. (d) Zoltewicz, J. A.; Uray, G. J. Org. Chem. 1980, 45, 2104.
36. For the ring opening of thiazoliun salts with nucleophiles, see: (a) Duclos J. M.; Haake, P. Biochemistry 1974, 13, 5358. (b) Hajós, Gy.; Messmer, A. J. J. Heterocycl. Chem. 1984, 21, 809. (c) Singh, H.; Lal, K. J. Chem. Soc., Perkin Trans. 1 1972, 1799. (d) Zoltewicz, J. A.; Uray, G. J. Org. Chem. 1980, 45, 2104.
37. For the ring opening of thiazoliun salts with nucleophiles, see: (a) Duclos J. M.; Haake, P. Biochemistry 1974, 13, 5358. (b) Hajós, Gy.; Messmer, A. J. J. Heterocycl. Chem. 1984, 21, 809. (c) Singh, H.; Lal, K. J. Chem. Soc., Perkin Trans. 1 1972, 1799. (d) Zoltewicz, J. A.; Uray, G. J. Org. Chem. 1980, 45, 2104.
38. For selected reviews, see: (a) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534. (b) Johnson J. S. Angew. Chem., Int. Ed. 2004, 43, 1326.
39. For selected reviews, see: (a) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534. (b) Johnson J. S. Angew. Chem., Int. Ed. 2004, 43, 1326.
40. (a) Stetter, H.; Kuhlman, H. Chem. Ber. 1976, 2890.
41. (b) Stetter, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 639.
42. (c) Stetter, H.; Kuhlmann, H. In Organic Reactions; Paquette, L. A., Ed.; Wiley and Sons: New York, 1991; Vol. 40.
43. (d) Harrington, P. E.; Tius, M. A. Org. Lett. 1999, 1, 649.
44. (e) Hempenius, M. A.; Langeveld-Voss, B. M. W.; van Haare, J. A. E. H.; Janssen, R. A. J.; Sheiko, S. S.; Spatz, J. P.; Moller, M.; Meijer, E. W. J. Am. Chem. Soc. 1998, 120, 2798.
45. (f) Murry, J. A.; Frantz, D. E. Soheili, A.; Tillyer, R.; Grabowski, E. J. J.; Paul, J.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 9696.
46. (g) Mattson, A. E.; Bharadwaj, A. R.; Scheidt, K. A. J. Am. Chem. Soc. 2004, 126, 2314.
47. For recent reviews on multicomponent reactions, see: (a) Weber, L.; Illgen, K.; Almstetter, M. Synlett 1999, 366. (b) Dömling A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3169. (c) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. (d) Zhu, J. P. Eur. J. Org. Chem. 2003, 1133.
48. For recent reviews on multicomponent reactions, see: (a) Weber, L.; Illgen, K.; Almstetter, M. Synlett 1999, 366. (b) Dömling A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3169. (c) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. (d) Zhu, J. P. Eur. J. Org. Chem. 2003, 1133.
49. For recent reviews on multicomponent reactions, see: (a) Weber, L.; Illgen, K.; Almstetter, M. Synlett 1999, 366. (b) Dömling A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3169. (c) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. (d) Zhu, J. P. Eur. J. Org. Chem. 2003, 1133.
50. For recent reviews on multicomponent reactions, see: (a) Weber, L.; Illgen, K.; Almstetter, M. Synlett 1999, 366. (b) Dömling A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3169. (c) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. (d) Zhu, J. P. Eur. J. Org. Chem. 2003, 1133.
51. For example, see: Motesharei, K.; Myles, D. C. J. Am. Chem. Soc. 1997, 119, 6674.
52. Only trace benzoin condensation product was found in the reaction mixture.
53. 13C NMR signals for the two ester carbonyls were seen at δ 165.20 and 164.62 ppm; see ref 4a.
54. It should be noted that in entries 10-13 no further attempt was made to optimize these reactions
55. Several papers have mentioned this similar type of bond breaking between carbon and heteroatoms in the heterocyclic systems; see selective references: (a) Kim, D. J.; Yoo, K. H.; Park, S. W. J. Org. Chem. 1992, 57, 2347. (b) Musicki, B. J. Org. Chem. 1990, 55, 910. (c) Meth-Cohn, O. Tetrahedron Lett. 1975, 16, 413. (d) Abe, N.; Nishiwaki, T.; Komoto, N. Bull. Chem. Soc. Jpn. 1980, 53, 3308. (e) Potts, K. T.; Choudhury, D. R.; Westby, T. R. J. Org. Chem. 1976, 41, 187.
56. Several papers have mentioned this similar type of bond breaking between carbon and heteroatoms in the heterocyclic systems; see selective references: (a) Kim, D. J.; Yoo, K. H.; Park, S. W. J. Org. Chem. 1992, 57, 2347. (b) Musicki, B. J. Org. Chem. 1990, 55, 910. (c) Meth-Cohn, O. Tetrahedron Lett. 1975, 16, 413. (d) Abe, N.; Nishiwaki, T.; Komoto, N. Bull. Chem. Soc. Jpn. 1980, 53, 3308. (e) Potts, K. T.; Choudhury, D. R.; Westby, T. R. J. Org. Chem. 1976, 41, 187.
57. Several papers have mentioned this similar type of bond breaking between carbon and heteroatoms in the heterocyclic systems; see selective references: (a) Kim, D. J.; Yoo, K. H.; Park, S. W. J. Org. Chem. 1992, 57, 2347. (b) Musicki, B. J. Org. Chem. 1990, 55, 910. (c) Meth-Cohn, O. Tetrahedron Lett. 1975, 16, 413. (d) Abe, N.; Nishiwaki, T.; Komoto, N. Bull. Chem. Soc. Jpn. 1980, 53, 3308. (e) Potts, K. T.; Choudhury, D. R.; Westby, T. R. J. Org. Chem. 1976, 41, 187.
58. Several papers have mentioned this similar type of bond breaking between carbon and heteroatoms in the heterocyclic systems; see selective references: (a) Kim, D. J.; Yoo, K. H.; Park, S. W. J. Org. Chem. 1992, 57, 2347. (b) Musicki, B. J. Org. Chem. 1990, 55, 910. (c) Meth-Cohn, O. Tetrahedron Lett. 1975, 16, 413. (d) Abe, N.; Nishiwaki, T.; Komoto, N. Bull. Chem. Soc. Jpn. 1980, 53, 3308. (e) Potts, K. T.; Choudhury, D. R.; Westby, T. R. J. Org. Chem. 1976, 41, 187.
59. Several papers have mentioned this similar type of bond breaking between carbon and heteroatoms in the heterocyclic systems; see selective references: (a) Kim, D. J.; Yoo, K. H.; Park, S. W. J. Org. Chem. 1992, 57, 2347. (b) Musicki, B. J. Org. Chem. 1990, 55, 910. (c) Meth-Cohn, O. Tetrahedron Lett. 1975, 16, 413. (d) Abe, N.; Nishiwaki, T.; Komoto, N. Bull. Chem. Soc. Jpn. 1980, 53, 3308. (e) Potts, K. T.; Choudhury, D. R.; Westby, T. R. J. Org. Chem. 1976, 41, 187.