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Volumn 127, Issue 25, 2005, Pages 8964-8965

Thiourea-catalyzed enantioselective cyanosilylation of ketones

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID; SCHIFF BASE; THIOUREA DERIVATIVE; UREA DERIVATIVE;

EID: 21244472590     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja052511x     Document Type: Article
Times cited : (336)

References (48)
  • 21
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    • (b) Tetrahedron Lett. 1995, 36, 6647-6650.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 6647-6650
  • 29
    • 0000140586 scopus 로고    scopus 로고
    • For a review on the synthetic utility of cyanohydrins see: Gregory, R. J. H. Chem. Rev. 1999, 99, 3649-3682.
    • (1999) Chem. Rev. , vol.99 , pp. 3649-3682
    • Gregory, R.J.H.1
  • 30
    • 3242810683 scopus 로고    scopus 로고
    • For an excellent recent review on the catalytic asymmetric cyanation of aldehydes and ketones see: Brunel, J.-M.; Holmes, I. P. Angew. Chem., Int. Ed. 2004, 43, 2752-2778.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 2752-2778
    • Brunel, J.-M.1    Holmes, I.P.2
  • 39
    • 21244470780 scopus 로고    scopus 로고
    • note
    • For a complete list of all urea and thiourea catalysts examined see the Supporting Information.
  • 40
    • 37049069958 scopus 로고
    • The role of the alcohol additive is presumably to generate HCN as the active nucleophile in the addition reaction, as is the case in thiourea-catalyzed Strecker reactions (ref 4). For other examples of the beneficial effect of alcohol additives on cyanosilylation of carbonyls see: (a) Hayashi, M.; Matsuda, N.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1992, 3135-3140.
    • (1992) J. Chem. Soc., Perkin Trans. 1 , pp. 3135-3140
    • Hayashi, M.1    Matsuda, N.2    Oguni, N.3
  • 42
    • 21244492408 scopus 로고    scopus 로고
    • Reference 15d
    • (c) Reference 15d.
  • 43
    • 21244441107 scopus 로고    scopus 로고
    • note
    • The corresponding N,N-di-n-butylamine- and N,N,-di-n-pentylamine- substituted catalysts afforded comparable conversion to 3d, but with slightly lower enantioselectivity (95%).
  • 44
    • 21244464409 scopus 로고    scopus 로고
    • note
    • For the preparation of 3d, see the Supporting Information.
  • 45
    • 21244506286 scopus 로고    scopus 로고
    • note
    • Dialkyl ketones are poor substrates in cyanosilylation reactions with 3d: 2-heptanone, 11% ee; cyclohexyl methyl ketone, <5% conversion.
  • 46
    • 0028802842 scopus 로고
    • Ketone enantioface selectivity dictated solely by electronic differentiation is well-precedented: (a) Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1995, 36, 9153-9156.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 9153-9156
    • Corey, E.J.1    Helal, C.J.2
  • 48
    • 21244494926 scopus 로고    scopus 로고
    • note
    • The cyclohexylamine-derived analogue of 3d, which lacks the tertiary amine group, displayed no reactivity under the standard conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.