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Volumn 130, Issue 44, 2008, Pages 14416-14417

Chiral squaramide derivatives are excellent hydrogen bond donor catalysts

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE;

EID: 55549133297     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja805693p     Document Type: Article
Times cited : (847)

References (36)
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    • Connon, S. J. Chem. - Eur. J. 2006, 12, 5418. See also ref 1.
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    • Examples of reactions catalyzed by chiral thioureas include the Strecker reaction: (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
    • Examples of reactions catalyzed by chiral thioureas include the Strecker reaction: (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
  • 5
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    • Michael addition: (b) Hoashi, Y.; Okino, T.; Takemoto, Y. Angew. Chem., Int. Ed. 2005, 44, 4032.
    • Michael addition: (b) Hoashi, Y.; Okino, T.; Takemoto, Y. Angew. Chem., Int. Ed. 2005, 44, 4032.
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    • Morita-Baylis-Hillman reaction: Wang, J.; Li, H.; Yu, X. H.; Zu, L. S.; Wang, W. Org. Lett. 2005, 7, 4293.
  • 8
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    • Friedel-Crafts reaction: Wang, Y. Q.; Song, J.; Hong, R.; Li, H. M.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8156.
    • (d) Friedel-Crafts reaction: Wang, Y. Q.; Song, J.; Hong, R.; Li, H. M.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8156.
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    • Petasis reaction: (e) Yamaoka, Y.; Miyabe, H.; Takemoto, Y. J. Am. Chem. Soc 2007, 129, 6686.
  • 10
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    • Pictet-Spengler cyclization : (f) Raheem, I. T.; Thiara, P. S.; Peterson, E. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 13404
  • 11
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    • Diels-Alder reaction: (g) Singh, R. P.; Bartelson, K.; Wang, Y.; Su, H.; Lu, X.; Deng, L. J. Am. Chem. Soc. 2008, 130, 2422.
    • Diels-Alder reaction: (g) Singh, R. P.; Bartelson, K.; Wang, Y.; Su, H.; Lu, X.; Deng, L. J. Am. Chem. Soc. 2008, 130, 2422.
  • 12
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    • Other chiral H-bond donor scaffolds include, inter alia, cinchona alkaloid derivatives: (a) Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 417.
    • Other chiral H-bond donor scaffolds include, inter alia, cinchona alkaloid derivatives: (a) Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 417.
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    • Structures were optimized with Hartree-Fock calculations using the 6-31G* basis set (Spartan '04 for Macintosh, Wavefunction, Inc.). The calculated H-H distance in the thiourea approximates that found in the crystal structure of Takemoto's thiourea catalyst: Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X. N.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119.
    • Structures were optimized with Hartree-Fock calculations using the 6-31G* basis set (Spartan '04 for Macintosh, Wavefunction, Inc.). The calculated H-H distance in the thiourea approximates that found in the crystal structure of Takemoto's thiourea catalyst: Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X. N.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119.
  • 21
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    • Squaramides have been used in molecular recognition studies: (a) Tomas, S.; Prohens, R.; Vega, M.; Rotger, M. C..; Deya, P. M.; Ballester, P.; Costa, A. J. Org. Chem. 1996, 61, 9394.
    • Squaramides have been used in molecular recognition studies: (a) Tomas, S.; Prohens, R.; Vega, M.; Rotger, M. C..; Deya, P. M.; Ballester, P.; Costa, A. J. Org. Chem. 1996, 61, 9394.
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    • Squaramides have been recognized as bioisosteres of ureas: Merritt, J. R.; Rokosz, L. L.; Kingsley, H. N.; Kaiser, B.; Wang, W.; Stauffer, T. M.; Ozgur, L. E.; Schilling, A.; Li, G.; Baldwin, J. J.; Taveras, A. G.; Dwyer, M. P.; Chao, J. P Bioorg. Med. Chem. Lett. 2006, 16, 4107.
    • Squaramides have been recognized as bioisosteres of ureas: Merritt, J. R.; Rokosz, L. L.; Kingsley, H. N.; Kaiser, B.; Wang, W.; Stauffer, T. M.; Ozgur, L. E.; Schilling, A.; Li, G.; Baldwin, J. J.; Taveras, A. G.; Dwyer, M. P.; Chao, J. P Bioorg. Med. Chem. Lett. 2006, 16, 4107.
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    • Chem. Soc, Please see Supporting Information for more details
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    • (2003) J. Am , vol.125 , pp. 12672
    • Okino, T.1    Hoashi, Y.2    Takemoto, Y.3
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    • Previous reports of organocatalytic conjugate additions of 1,3-dicarbonyl compounds to nitroolefins include: (a) Li, H. M.; Wang, Y.; Tang, L.; Deng, L. J. Am. Chem. Soc. 2004, 126, 9906.
    • Previous reports of organocatalytic conjugate additions of 1,3-dicarbonyl compounds to nitroolefins include: (a) Li, H. M.; Wang, Y.; Tang, L.; Deng, L. J. Am. Chem. Soc. 2004, 126, 9906.
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    • The absolute stereochemistry of 8 was assigned by comparison of the optical rotation with the value determined in ref 9e.
    • The absolute stereochemistry of 8 was assigned by comparison of the optical rotation with the value determined in ref 9e.


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