3-trifluoromethanesulfonamido-Pyrrolidine: A general organocatalyst for antf-selective mannich reactions

Organic Letters

Volumn 10, Issue 5, 2008, Pages 1029-1032

  Pouliquen, Mickael ^a   Blanchet, Jérome ^a   Lasne, Marie Claire ^a   Rouden, Jacques ^a  

^a UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 51749116225     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8000975     Document Type: Article

References (44)

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38. This work was presented at the Journées de Chimie Organique 2007, Palaiseau, France, on 19th September 2007 (Société Francaise de Chimie).
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42. To the best of our knowledge, such 3-centered hydrogen bonding has not been proposed nor ruled out by computational studies. This unusual interaction is a generally accepted concept. See Jeff'rev, G. A.; Mitra. J. J. Am. Chem. Soc. 1984,' 106, 5546-5553 and Okamoto. I.; Nabeta, M.; Hayakawa, Y.; Morita, N.; Takeya, T.; Masu, H.; Azumaya, I.; Tamura, O. J. Am. Chem. Soc. 2007, 129. 1892-1893. One reviewer is aknowledged to have drawn our attention on this point.
43. 1H NMR shifts, and absolute configuration was assigned by direct comparison of the sign of optical rotation with reported data (see ref 8). HPLC peaks of anti- and syn-diastereorners were attributed by carrying out syn-Maimich reaction with proline. Absolute configuration of the syn-diastereomer was not determined.
44. Cyclohexane carboxaldehyde and cyclopentane carboxaldehyde gave respectively 55% ee and 98% ee with 30 mol % proline in DMSO at room temperature, see: Chowdari, N. S.; Suri, J. T.; Barbas. C. F., III. Org. Lett., 2004, 6, 2507-2510.