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Volumn 350, Issue 18, 2008, Pages 2877-2880

Catalyst-free aldol additions of 1,3-dicarbonyl compounds

Author keywords

1,3 dicarbonyl compounds; Aldehydes; Aldol reaction; Quaternary stereocenters; Solvent free reaction

Indexed keywords


EID: 57849099641     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800554     Document Type: Article
Times cited : (34)

References (33)
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    • For aldol additions of malonates in total synthesis of epolactaene, see
    • a) For aldol additions of malonates in total synthesis of epolactaene, see: S. Marumoto, H. Kogen, S. Naruto, J. Org. Chem. 1998, 63, 2068-2069;
    • (1998) J. Org. Chem , vol.63 , pp. 2068-2069
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  • 2
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    • for aldol additions of malonates in the total synthesis of carbohydrates, see
    • b) for aldol additions of malonates in the total synthesis of carbohydrates, see: A. Saba, V. Adovasio, M. Nardelli, Tetrahedron: Asymmetry 1992, 3, 1573-1582.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 1573-1582
    • Saba, A.1    Adovasio, V.2    Nardelli, M.3
  • 4
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    • acetoacetic ethyl ester in the presence of triethylamine, see: J. W. Cornforth, J. E. Hawes, German Patent DE 2336394, 1974;
    • b) acetoacetic ethyl ester in the presence of triethylamine, see: J. W. Cornforth, J. E. Hawes, German Patent DE 2336394, 1974;
  • 5
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    • for hydroxymethylation of 2-oxocyclohexane- and 2- oxocyclopentanecarboxylic acid esters in the presence of
    • c) for hydroxymethylation of 2-oxocyclohexane- and 2- oxocyclopentanecarboxylic acid esters in the presence of CaO, see: H. Gerdes, H. Marschall, P. Weyerstahl, Chem. Ber. 1975, 108, 3448-3460;
    • (1975) Chem. Ber , vol.108 , pp. 3448-3460
    • CaO1    see2    Gerdes, H.3    Marschall, H.4    Weyerstahl, P.5
  • 6
    • 57849083673 scopus 로고    scopus 로고
    • for hydroxymethylation of 2.4-pentanedione in the presence of KOH, see: J. J. Gyuran, European Patent EP 350320, 1990;
    • d) for hydroxymethylation of 2.4-pentanedione in the presence of KOH, see: J. J. Gyuran, European Patent EP 350320, 1990;
  • 7
    • 0030829742 scopus 로고    scopus 로고
    • for hydroxymethylation of malonates, see
    • e) for hydroxymethylation of malonates, see: A. Guzaev, H. Lönnberg, Synthesis 1997, 1281-1284;
    • (1997) Synthesis , pp. 1281-1284
    • Guzaev, A.1    Lönnberg, H.2
  • 8
    • 0032565996 scopus 로고    scopus 로고
    • for hydroxymethylation of a-methyl-substituted acetoacetic ethyl ester, see
    • f) for hydroxymethylation of a-methyl-substituted acetoacetic ethyl ester, see: T. Akeboshi, Y. Ohtsuka, T. Sugai, H. Ohta, Tetrahedron 1998, 54, 7387-7394;
    • (1998) Tetrahedron , vol.54 , pp. 7387-7394
    • Akeboshi, T.1    Ohtsuka, Y.2    Sugai, T.3    Ohta, H.4
  • 9
    • 34247228673 scopus 로고    scopus 로고
    • for iron-catalyzed hydroxymethylation, see
    • g) for iron-catalyzed hydroxymethylation, see C. Ogawa, S. Kobayashi, Chem. Lett. 2007, 36, 56-57.
    • (2007) Chem. Lett , vol.36 , pp. 56-57
    • Ogawa, C.1    Kobayashi, S.2
  • 14
    • 37749043974 scopus 로고    scopus 로고
    • For an aldol addition of aqueous formaldehyde with bicyclic β-keto ester, see
    • For an aldol addition of aqueous formaldehyde with bicyclic β-keto ester, see: S. Shirakawa, S. Shimizu, Synlett 2007, 3160-3164.
    • (2007) Synlett , pp. 3160-3164
    • Shirakawa, S.1    Shimizu, S.2
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    • Angew. Chem. Int. Ed. 2008, 47, 4196-4199.
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 4196-4199
  • 29
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    • We call this reaction unexpected because this exceptional behaviour of activated aldehydes was not predictable; see also: S. Shirakawa, K. Maruoka, Tetrahedron Lett. 2003, 44, 281-284.
    • We call this reaction "unexpected" because this exceptional behaviour of activated aldehydes was not predictable; see also: S. Shirakawa, K. Maruoka, Tetrahedron Lett. 2003, 44, 281-284.
  • 30
    • 57849084990 scopus 로고    scopus 로고
    • 2,2-Dimethoxyacetaldehyde 1b (60%) and chloroacetaldehyde 1c (50%) were deployed as aqueous solutions, (R)- and (S)-menthyl glyoxylates 1f and 1g were used as monohydrates, whereas ethyl glyoxalate 1a was applied as a solution in toluene (50%).
    • 2,2-Dimethoxyacetaldehyde 1b (60%) and chloroacetaldehyde 1c (50%) were deployed as aqueous solutions, (R)- and (S)-menthyl glyoxylates 1f and 1g were used as monohydrates, whereas ethyl glyoxalate 1a was applied as a solution in toluene (50%).
  • 32
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    • This stereochemical result was not described in ref.[17
    • [17]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.