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Volumn 71, Issue 16, 2006, Pages 6269-6272

Direct access to enantiomerically enriched α-amino phosphonic acid derivatives by organocatalytic asymmetric hydrophosphonylation of imines

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CATALYSIS; DERIVATIVES; NITROGEN COMPOUNDS; PHOSPHORUS COMPOUNDS;

EID: 33746889829     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060708h     Document Type: Article
Times cited : (143)

References (38)
  • 1
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    • 0003563365 scopus 로고    scopus 로고
    • Kukhar, V. P., Hudson, H. R., Eds.; John Wiley & Sons: New York
    • (d) Aminophosphonic and Aminophosphinic Acids; Kukhar, V. P., Hudson, H. R., Eds.; John Wiley & Sons: New York, 2000.
    • (2000) Aminophosphonic and Aminophosphinic Acids
  • 18
    • 0009354916 scopus 로고    scopus 로고
    • (d) Weimer, D. F. Tetrahedron 1997, 53, 16609-16644.
    • (1997) Tetrahedron , vol.53 , pp. 16609-16644
    • Weimer, D.F.1
  • 19
    • 23544442924 scopus 로고    scopus 로고
    • Helmchen, G., Hoffmann, R.-W., Mulzer, J., Schumann, E., Eds.; Thieme Verlag: Stuttgart, and references therein
    • (e) Mikołajczyk, M.; Drabowicz, J.; Kiełbasinski, P. In Stereoselective Synthesis (Houben-Weyl); Helmchen, G., Hoffmann, R.-W., Mulzer, J., Schumann, E., Eds.; Thieme Verlag: Stuttgart, 1996; Vol. E 21e, pp 5701-5712 and references therein.
    • (1996) Stereoselective Synthesis (Houben-Weyl) , vol.E 21E , pp. 5701-5712
    • Mikołajczyk, M.1    Drabowicz, J.2    Kiełbasinski, P.3
  • 27
  • 31
    • 0001591182 scopus 로고
    • For quinine-catalyzed addition of phosphites to aldehydes, see: (a) Wynberg, H.; Smaardijk, A. A. Tetrahedron Lett. 1983, 24, 5899-5900.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 5899-5900
    • Wynberg, H.1    Smaardijk, A.A.2
  • 33
    • 33746896497 scopus 로고    scopus 로고
    • note
    • Several cinchona-derived catalysts with an acidic proton moiety were tested and found to be inferior to quinine and quinidine.
  • 34
    • 33746895734 scopus 로고    scopus 로고
    • note
    • Using a Cbz-protected imine gave a product with lower enantioselectivity compared to the analogous Boc-protected imine. This observation in combination with the more tedious preparation of Cbz imines resulted in no further consideration of Cbz imines as substrates.
  • 35
    • 33746873202 scopus 로고    scopus 로고
    • note
    • A screening of solvents showed that xylene gave better results than, e.g., toluene and polar protic and aprotic solvents. Use of fluorobenzene or mesitylene lowered the selectivity with respect to xylene. No difference could be observed between using a mixture of xylenes or p-xylene as solvent.
  • 37
    • 33746888580 scopus 로고    scopus 로고
    • note
    • Changing the nucleophile to diisopropyl phosphite lowered the reactivity and selectivity of the reaction, whereas dimethyl phosphite was unreactive.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.