메뉴 건너뛰기




Volumn 67, Issue 25, 2002, Pages 8928-8937

Diastereoselective aldolization of α-aminonitriles. Diastereoselective synthesis of β-amino alcohols and β,γ-diamino alcohols

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOSELECTIVITY;

EID: 0037073874     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo025872t     Document Type: Article
Times cited : (26)

References (49)
  • 10
    • 0001409660 scopus 로고    scopus 로고
    • (c) Carlier, P. R.; Moon Lo, K.; Lo, M. M.-C.; Lo, P. C.-K.; Lo, C. W.-S. J. Org. Chem. 1997, 62, 6316-6321. Mecozzi, T., Petrini, M., Profeta, R. J. Org. Chem. 2001, 66, 8264-8267. Carlier, P. R., Madura, J. D. J. Org. Chem. 2002, 67, 3832-3840.
    • (1997) J. Org. Chem. , vol.62 , pp. 6316-6321
    • Carlier, P.R.1    Moon Lo, K.2    Lo, M.M.-C.3    Lo, P.C.-K.4    Lo, C.W.-S.5
  • 11
    • 0035977218 scopus 로고    scopus 로고
    • (c) Carlier, P. R.; Moon Lo, K.; Lo, M. M.-C.; Lo, P. C.-K.; Lo, C. W.-S. J. Org. Chem. 1997, 62, 6316-6321. Mecozzi, T., Petrini, M., Profeta, R. J. Org. Chem. 2001, 66, 8264-8267. Carlier, P. R., Madura, J. D. J. Org. Chem. 2002, 67, 3832-3840.
    • (2001) J. Org. Chem. , vol.66 , pp. 8264-8267
    • Mecozzi, T.1    Petrini, M.2    Profeta, R.3
  • 12
    • 0037204919 scopus 로고    scopus 로고
    • (c) Carlier, P. R.; Moon Lo, K.; Lo, M. M.-C.; Lo, P. C.-K.; Lo, C. W.-S. J. Org. Chem. 1997, 62, 6316-6321. Mecozzi, T., Petrini, M., Profeta, R. J. Org. Chem. 2001, 66, 8264-8267. Carlier, P. R., Madura, J. D. J. Org. Chem. 2002, 67, 3832-3840.
    • (2002) J. Org. Chem. , vol.67 , pp. 3832-3840
    • Carlier, P.R.1    Madura, J.D.2
  • 17
    • 0034602234 scopus 로고    scopus 로고
    • (d) Badorrey, R., Cativiela, C., Diaz-de-Villegas, M. D., Galvez, J. A. A. Tetrahedron: Asymmetry 2000, 11, 1015-1025. Davis, F. A., Sriraja, V., Fanelli, D. L., Portonovo, P. J. Org. Chem. 2000, 65, 7663-7666.
    • (2000) J. Org. Chem. , vol.65 , pp. 7663-7666
    • Davis, F.A.1    Sriraja, V.2    Fanelli, D.L.3    Portonovo, P.4
  • 22
    • 2242464188 scopus 로고    scopus 로고
    • note
    • Crystallographic data for the strustural analysis have been deposited with the Cambridge Crystallographic Data Center, CCDC No. 178177.
  • 23
    • 2242474110 scopus 로고    scopus 로고
    • note
    • 1H NMR were found to be higher for all the minor (syn) diastereomers than the corresponding ones observed for the major (anti) diastereomers; see ref 4.
  • 25
    • 2242457868 scopus 로고    scopus 로고
    • note
    • Crystallographic data for the strustural analysis have been deposited with the Cambridge Crystallographic Data Center, CCDC No. 178048.
  • 28
    • 0036135888 scopus 로고    scopus 로고
    • Enders, D.; Kirchhoff, J.; Gerdes, P.; Mannes, D.; Raabe, G.; Runsink, J.; Boche, G.; Marsch, M.; Ahlbrecht, H.; Sommer, H. Eur. J. Org. Chem. 1998, 63, 3-72. Fleming, F. F., Shook, B. C. Tetrahedron 2002, 58, 1-23.
    • (2002) Tetrahedron , vol.58 , pp. 1-23
    • Fleming, F.F.1    Shook, B.C.2
  • 31
    • 2242420202 scopus 로고    scopus 로고
    • note
    • As suggested by one of our reviewers, one may involve a transition state where the two N-substituents are roughly in the plane of the keteniminate, with the t-Bu group exo and the benzyl endo (see structure below). Such conformation would reduce steric congestion in the transition state energy, thereby negating the effect of any ground-state destabilization.
  • 32
    • 84985502354 scopus 로고
    • These two experiments were run in order to perform a pseudo-Hoffmann test due to the possible but improbable configurational stability of lithiated α-aminonitriles. Hoffmann, R.; Lanz, J.; Metternich, R.; Tarara, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1987, 26, 1145-1146.
    • (1987) Angew. Chem., Int. Ed. Engl. , vol.26 , pp. 1145-1146
    • Hoffmann, R.1    Lanz, J.2    Metternich, R.3    Tarara, G.4    Hoppe, D.5
  • 33
    • 0034613348 scopus 로고    scopus 로고
    • (a) Similar results were obtained with configurationally stable allenyl zinc reagents: Poisson, J. F.; Normant, J. F. J. Org. Chem. 2000, 65, 6553-6560.
    • (2000) J. Org. Chem. , vol.65 , pp. 6553-6560
    • Poisson, J.F.1    Normant, J.F.2
  • 34
  • 35
    • 2242424689 scopus 로고    scopus 로고
    • note
    • Crystallographic data for the structural analysis have been deposited with the Cambridge Crystallographic Data Center, CCDC No. 178047.
  • 36
    • 2242438273 scopus 로고    scopus 로고
    • note
    • The modest selectivity obtained with chiral aldehydes 12 and 13 is in accordance with the results generally obtained with these aldehydes. Moreover, it is possible that, due to the cyclic nature of the transition state, the attack of the lithiated ketene imine to the aldehyde does not occur in the Bürgi-Dunitz angle, which is important for the selectivity (see ref 18b).
  • 39
    • 2242418413 scopus 로고    scopus 로고
    • The addition of Grignard reagents to the nitrile is surprising in the light of the Bruylants reaction. Such chemioselectivity is probably due to the steric effect of the t-Bu group, which prevents the formation of the immoniun intermediate. Indeed, we have observed that addition of BuMgBr to an aldol derived from 4 yielded exclusively to the Bruylants's product. Moreover, we also found that it was possible to perform the Bruylants reaction by addition of Grignard reagents to the immoniums derived from aldols 10d,e as described by Couty and Agami: Agami, C, Couty, F., Ewano, G Org. Lett. 2000, 2, 2065-2088.
    • (2000) Org. Lett. , vol.2 , pp. 2065-2088
    • Agami, C.1    Couty, F.2    Ewano, G.3
  • 40
    • 2242490220 scopus 로고    scopus 로고
    • note
    • Crystallographic data for the structural analysis have been deposited with the Cambridge Crystallographic Data Center, CCDC No. 178176 for 16c and CCDC No. 178175 for 16d.
  • 42
  • 44
    • 2242477727 scopus 로고    scopus 로고
    • note
    • 2 protected derivative did not occur.
  • 46
    • 0001301921 scopus 로고
    • For the cleavage of an N-tert-butyl group on a secondary amine, see: De Kimpe, N.; Sulmon, P.; Brunet, P. J. Org. Chem. 1990, 55. 5777-5784. Bundy, G. I.; Banitt, L. S.; Dobrowolski, P. J.; Palmer, J. R.; Schwartz, T. M.; Zimmermann, D. C.; Lipton, M. F.; Mauragis, M. A.; Veley, M. F.; Appell, R. B.; Clouse, R. C.; Daug, E. D. Org. Process Dev. 2001, 5, 144-151.
    • (1990) J. Org. Chem. , vol.55 , pp. 5777-5784
    • De Kimpe, N.1    Sulmon, P.2    Brunet, P.3
  • 48
    • 2242481323 scopus 로고    scopus 로고
    • WO Patent 9636602, 1996
    • Sachs, M. WO Patent 9636602, 1996.
    • Sachs, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.