메뉴 건너뛰기




Volumn 71, Issue 6, 2006, Pages 2538-2541

Erratum: Mild organocatalytic α-methylenation of aldehydes (Journal of Organic Chemistry (2006) 71: 6 (2538-2541) DOI: 10.1021/jo052529q);Mild organocatalytic α-methylenation of aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; FORMALDEHYDE; METHANOL; SOLUTIONS;

EID: 33645035198     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401861r     Document Type: Erratum
Times cited : (116)

References (49)
  • 9
  • 10
    • 0037139610 scopus 로고    scopus 로고
    • α,β-Unsaturated aldehydes are key starting materials for several organocatalytic transformations utilizing iminium catalysis. For representative examples, see the following. Diels-Alder reaction: (a) Northrup, A. B.; MacMillan, D. W. E. J. Am. Chem. Soc. 2002, 124, 2458-2460.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 2458-2460
    • Northrup, A.B.1    MacMillan, D.W.E.2
  • 14
    • 23044486704 scopus 로고    scopus 로고
    • Very recently, α-substituted α,β-unsaturated aldehydes have also emerged as viable partners for iminium catalysis: (e) Ishihara, K.; Nakano, K. J. Am. Chem. Soc. 2005, 127, 10504-10505.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 10504-10505
    • Ishihara, K.1    Nakano, K.2
  • 17
    • 33645026119 scopus 로고    scopus 로고
    • JP 04173757, 1992
    • (b) Matsuoka, K. JP 04173757, 1992.
    • Matsuoka, K.1
  • 18
    • 33645022963 scopus 로고    scopus 로고
    • JP 06263683, 1994. JP3324820, 2002
    • (c) Nagareda, K.; Yoshimura, N. JP 06263683, 1994. JP3324820, 2002.
    • Nagareda, K.1    Yoshimura, N.2
  • 25
    • 0000388074 scopus 로고
    • This paper also includes an excellent introduction to the state-of-the-art methods for the synthesis of α-substituted acroleins. (7) For experimental examples with more complex aldehydes, see: (a) Yoshida, K.; Grieco, P. J. Org. Chem. 1984, 49, 5257-5260.
    • (1984) J. Org. Chem. , vol.49 , pp. 5257-5260
    • Yoshida, K.1    Grieco, P.2
  • 27
    • 33645030162 scopus 로고    scopus 로고
    • note
    • (c) In our hands, these protocols often failed to give any useful yields of the product, especially with aldehydes prone to polymerization.
  • 40
    • 14844344225 scopus 로고    scopus 로고
    • Recently, an organocatalytic method for the synthesis of α,β-unsaturated ketones was reported: (a) Wang, W.; Mei, Y.; Li, H.; Wang, J. Org. Lett. 2005, 7, 601-604.
    • (2005) Org. Lett. , vol.7 , pp. 601-604
    • Wang, W.1    Mei, Y.2    Li, H.3    Wang, J.4
  • 41
    • 3142720242 scopus 로고    scopus 로고
    • (a) Córdova and co-workers have reported that reactions between aldehydes with formaldehyde under proline catalysis afford hydroxymethylated aldehydes enantioselectively. This would suggest that the reaction proceeds via an aldol-dehydration mechanism. However, in our hands reactions of aldehydes with aqueous formaldehyde only afforded the corresponding unsaturated aldehydes. Casas, J.; Sundén, H.; Córdova, A. Tetrahedron Lett. 2004, 45, 6117-6119.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 6117-6119
    • Casas, J.1    Sundén, H.2    Córdova, A.3
  • 42
    • 0032945520 scopus 로고    scopus 로고
    • (b) Interestingly, Ishikawa and co-workers have reported a pyrrolidine/benzoic acid catalyzed dimerization of aldehydes that proceeds at room temperature: Ishikawa, T.; Uedo, E.; Okada, S.; Saito, S. Synlett 1999, 4, 450-452.
    • (1999) Synlett , vol.4 , pp. 450-452
    • Ishikawa, T.1    Uedo, E.2    Okada, S.3    Saito, S.4
  • 43
  • 48
    • 33645022586 scopus 로고    scopus 로고
    • note
    • With simple amines, raising the temperature afforded higher conversions to the product. However, polymerization and loss of product by evaporation resulted in erratic and irreproducible yields in the case of methacrolein.
  • 49
    • 33645030054 scopus 로고    scopus 로고
    • note
    • With catalyst 4, 5-hydroxyvaleraldehyde gave ca. 55-60% yield of the α-methylenation product after 24 h reaction time, accompanied by significant decomposition. 2-Deoxyribose afforded less than 5% of the product under similar conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.