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Volumn 73, Issue 6, 2008, Pages 2446-2449

Robust and efficient, yet uncatalyzed, synthesis of trialkylsilyl-protected cyanohydrins from ketones

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL BONDS; NEGATIVE IONS; SODIUM COMPOUNDS; SYNTHESIS (CHEMICAL); TRANSIENT ANALYSIS;

EID: 41949124848     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702587e     Document Type: Article
Times cited : (25)

References (61)
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    • Wilkinson, H. S, Grover, P. T, Vandenbossche, C. P, Bakale, R. P, Bhongle, N. N, Wald, S. A, Senanayake, C. H. Org. Lett. 2001, 3, 553-556. We thank one of the reviewers for identifying a few relevant references
    • (k) Wilkinson, H. S.; Grover, P. T.; Vandenbossche, C. P.; Bakale, R. P.; Bhongle, N. N.; Wald, S. A.; Senanayake, C. H. Org. Lett. 2001, 3, 553-556. We thank one of the reviewers for identifying a few relevant references.
  • 39
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    • Silva, M. M. C.; Andrade, L. C. R.; Paixão, J. A.; Jose de Almeida, M.; Sá e Melo, M. L. Steroids 2005, 70, 145-151.
    • (p) Silva, M. M. C.; Andrade, L. C. R.; Paixão, J. A.; Jose de Almeida, M.; Sá e Melo, M. L. Steroids 2005, 70, 145-151.
  • 48
    • 84982465298 scopus 로고    scopus 로고
    • In one notable exception, a combination of KCN and TMSCl in DMF has been used: (a) Rasmussen, J. K.; Heilmann, S. M. Synthesis 1978, 219-221. However, application of DMF in industrial chemistry is undesirable due to its toxicity.
    • In one notable exception, a combination of KCN and TMSCl in DMF has been used: (a) Rasmussen, J. K.; Heilmann, S. M. Synthesis 1978, 219-221. However, application of DMF in industrial chemistry is undesirable due to its toxicity.
  • 49
    • 84988103404 scopus 로고    scopus 로고
    • Improvements of this method were later reported: (b) Duboudin, F.; Cazeau, P.; Moulines, F.; Lapone, O. Synthesis 1982, 212-214.
    • Improvements of this method were later reported: (b) Duboudin, F.; Cazeau, P.; Moulines, F.; Lapone, O. Synthesis 1982, 212-214.
  • 51
    • 18144411965 scopus 로고
    • In all cases, relatively long reaction times were required for unreactive carbonyl compounds
    • (d) Sukata, K. Bull. Chem. Soc. Jpn. 1987, 60, 3820-3822. In all cases, relatively long reaction times were required for unreactive carbonyl compounds.
    • (1987) Bull. Chem. Soc. Jpn , vol.60 , pp. 3820-3822
    • Sukata, K.1
  • 52
    • 41949088839 scopus 로고    scopus 로고
    • Dielectric constants, ε = 47.2 (DMSO); 38.8 (DMA); 38.2 (DMF); 36.6 (MeCN); 32.6 (NMP). See: Lide, D. R. In CRC Handbook of Chemistry and Physics, 81st ed.; CRC Press LLC: Boca Raton, 2000-2001; 6-149.
    • Dielectric constants, ε = 47.2 (DMSO); 38.8 (DMA); 38.2 (DMF); 36.6 (MeCN); 32.6 (NMP). See: Lide, D. R. In CRC Handbook of Chemistry and Physics, 81st ed.; CRC Press LLC: Boca Raton, 2000-2001; 6-149.
  • 54
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    • The nucleophilicity of small and soft cyanide anions is particularly augmented in DMSO; see: b
    • The nucleophilicity of small and soft cyanide anions is particularly augmented in DMSO; see: (b) Landini, D.; Maia, A.; Montanari, F. J. Am. Chem. Soc. 1978, 100, 2796-2801.
    • (1978) J. Am. Chem. Soc , vol.100 , pp. 2796-2801
    • Landini, D.1    Maia, A.2    Montanari, F.3
  • 56
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    • 5g
    • 5g
  • 59
    • 0141603738 scopus 로고    scopus 로고
    • It rules out an alternative mechanism that would involve nucleophilic catalysis by DMSO. The activation of a silyl group or a cyanoformate by coordination with the DMSO-oxygen was indeed suggested for the silylation of alcohols, and the cyanocarboxylation of aldehydes in DMSO respectively, see: a
    • It rules out an alternative mechanism that would involve nucleophilic catalysis by DMSO. The activation of a silyl group or a cyanoformate by coordination with the DMSO-oxygen was indeed suggested for the silylation of alcohols, and the cyanocarboxylation of aldehydes in DMSO respectively, see: (a) Watahiki, T.; Matsuzaki, M.; Oriyama, T. Green Chem. 2003, 5, 82-84.
    • (2003) Green Chem , vol.5 , pp. 82-84
    • Watahiki, T.1    Matsuzaki, M.2    Oriyama, T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.