메뉴 건너뛰기




Volumn 126, Issue 17, 2004, Pages 5356-5357

Chiral Brønsted Acid-Catalyzed Direct Mannich Reactions via Electrophilic Activation

Author keywords

[No Author keywords available]

Indexed keywords

ACID; PHOSPHORIC ACID DERIVATIVE;

EID: 2342521907     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0491533     Document Type: Article
Times cited : (1387)

References (66)
  • 5
  • 10
    • 0037134880 scopus 로고    scopus 로고
    • Recent examples of enantioselective organocatalysis via enamine formation. Aldol reactions: (a) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 6798
    • Northrup, A.B.1    MacMillan, D.W.C.2
  • 30
    • 0034807741 scopus 로고    scopus 로고
    • Other recent examples of secondary amine-catalyzed enantioselective carbon-carbon bond formation. Friedel-Crafts reactions: (a) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem Soc. 2001, 123, 4370.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 4370
    • Paras, N.A.1    MacMillan, D.W.C.2
  • 41
    • 1642369984 scopus 로고    scopus 로고
    • See also ref 6
    • Some other chiral charged Brønsted acid catalysts were reported, see: Nugent, B. M.; Yoder, R. A.; Johnston, J. N. J. Am. Chem. Soc. 2004, 126, 3418. See also ref 6.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 3418
    • Nugent, B.M.1    Yoder, R.A.2    Johnston, J.N.3
  • 51
    • 2342570203 scopus 로고    scopus 로고
    • During the preparation of this manuscript, Akiyama et al. reported similar phosphoric acid-catalyzed Mannich reactions between N-aryl protected imines and silyl ketene acetals. Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 1566
    • Akiyama, T.1    Itoh, J.2    Yokota, K.3    Fuchibe, K.4
  • 52
    • 1642415515 scopus 로고    scopus 로고
    • For an excellent review of catalytic asymmetric direct Mannich reactions, see: Córdova, A. Acc. Chem. Res. 2004, 37, 102.
    • (2004) Acc. Chem. Res. , vol.37 , pp. 102
    • Córdova, A.1
  • 54
    • 0037438599 scopus 로고    scopus 로고
    • Metal catalyst-mediated asymmetric direct Mannich reactions, see: (a) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 338
    • Trost, B.M.1    Terrell, L.R.2
  • 57
    • 0004231121 scopus 로고    scopus 로고
    • John Wiley & Sons: New York; Chapter 5
    • a of diethyl phosphate is 1.39. See: Quin, L. D. A Guide to Organophosphorus Chemistry; John Wiley & Sons: New York, 2000; Chapter 5, pp 133-165. The phosphodiester group has previously been found to provide highly efficient ionic hydrogen bonding sites, see: Bähr, A.; Felber, B.; Schneider, K.; Dieclerich F. Helv. Chim. Acta 2000, 83, 1346 and references therein.
    • (2000) A Guide to Organophosphorus Chemistry , pp. 133-165
    • Quin, L.D.1
  • 58
    • 0037744013 scopus 로고    scopus 로고
    • and references therein.
    • a of diethyl phosphate is 1.39. See: Quin, L. D. A Guide to Organophosphorus Chemistry; John Wiley & Sons: New York, 2000; Chapter 5, pp 133-165. The phosphodiester group has previously been found to provide highly efficient ionic hydrogen bonding sites, see: Bähr, A.; Felber, B.; Schneider, K.; Dieclerich F. Helv. Chim. Acta 2000, 83, 1346 and references therein.
    • (2000) Helv. Chim. Acta , vol.83 , pp. 1346
    • Bähr, A.1    Felber, B.2    Schneider, K.3    Dieclerich, F.4
  • 63
    • 2342528380 scopus 로고    scopus 로고
    • Eur. Pat. Appl. EP-A1-1038877, 2000
    • (e) Inanaga, J.; Furuno, H. Eur. Pat. Appl. EP-A1-1038877, 2000.
    • Inanaga, J.1    Furuno, H.2
  • 64
    • 2342482976 scopus 로고    scopus 로고
    • Eur. Pat. Appl. EP-A1-1134209, 2001
    • Binaphthol monophosphoric acid derivatives have been used as effective NMR shift reagent, see: Inanaga, J. Eur. Pat. Appl. EP-A1-1134209, 2001.
    • Inanaga, J.1
  • 65
    • 2342631824 scopus 로고    scopus 로고
    • note
    • 2O (97%, 88% ee).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.