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Volumn 70, Issue 14, 2005, Pages 5678-5687

Direct, facile aldehyde and ketone α-selenenylation reactions promoted by L-prolinamide and pyrrolidine sulfonamide organocatalysts

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; AMINES; HYDROGEN BONDS; KETONES;

EID: 84961985214     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0506940     Document Type: Article
Times cited : (91)

References (69)
  • 14
  • 15
  • 17
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    • Special issue: Asymmetric organocatalysis
    • (f) Special issue: Asymmetric organocatalysis. Acc. Chem. Res. 2004, 37, 487.
    • (2004) Acc. Chem. Res. , vol.37 , pp. 487
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    • 0034721440 scopus 로고    scopus 로고
    • For proline-catalyzed Mannich reactions, see: (a) List, B. J. Am. Chem. Soc. 2000, 122, 9336.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 9336
    • List, B.1
  • 33
    • 0037157154 scopus 로고    scopus 로고
    • For proline-catalyzed α-amination reactions, see: (a) List, B. J. Am. Chem. Soc. 2002, 124, 5656.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 5656
    • List, B.1
  • 40
    • 3042625080 scopus 로고    scopus 로고
    • Other organocatalysts have also been developed for catalysis via enamine chemistry; for selected examples, see: (a) Chiral diamine: Mase, N.; Tanaka, F.; Barbas, C. F., III Angew. Chem., Int. Ed. 2004, 43, 2420.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 2420
    • Mase, N.1    Tanaka, F.2    Barbas III, C.F.3
  • 46
    • 4344625961 scopus 로고    scopus 로고
    • The preliminary study of aldehyde α-selenenylations has been communicated in: Wang, W.; Wang, J.; Li, H. Org. Lett. 2004, 6, 2817.
    • (2004) Org. Lett. , vol.6 , pp. 2817
    • Wang, W.1    Wang, J.2    Li, H.3
  • 47
    • 14844316261 scopus 로고    scopus 로고
    • The (S) pyrrolidine trifluoromethanesulfonamide 2 has been demonstrated for the following reactions: (a) Michael addition: Wang, W.; Wang, J.; Li, H. Angew. Chem., Int. Ed. 2005, 44, 1369.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 1369
    • Wang, W.1    Wang, J.2    Li, H.3
  • 52
    • 13444267885 scopus 로고    scopus 로고
    • Recently, Jørgensen and co-workers reported an organocatalytic asymmetric α-sulfenylation, see: Marigo, M.; Wabnitz, T. C.; Fielenbach, D.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 794. They tested L-proline and L-prolinamide catalyzed α-sulfenylation of isovaleraldehyde with very poor enantioselectivity (0 and 25% ee in toluene, respectively).
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 794
    • Marigo, M.1    Wabnitz, T.C.2    Fielenbach, D.3    Jørgensen, K.A.4
  • 53
    • 84962335977 scopus 로고    scopus 로고
    • note
    • As cited in ref 16d, we have reported using (S) pyrrolidine trifluoromethanesulfonamide 2 as catalyst for α-sulfenylation reactions of aldehydes and ketones, unfortunately no enantioselectivities were observed for the processes.
  • 54
    • 84962342286 scopus 로고    scopus 로고
    • note
    • As reported in ref 17, Jørgensen and co-workers found that the bulk silylated L-prolinol derivatives as catalysts afforded α- sulfenylation products with high ee.
  • 62
    • 84962405500 scopus 로고    scopus 로고
    • note
    • Molecular sieves could retard the hydrolysis of iminium to release catalyst. However, this step is not the rate-determining step in the reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.