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Volumn 34, Issue 14, 2004, Pages 2591-2600

Synthesis of α-hydroxy ketones from terpene aldehydes

Author keywords

Hydroxy ketones; Acyloins; Camphanates; Copper salt catalysis; Cyanohydrin trimethylsilyl ethers; Grignard reaction; Nitriles; Tautomerisation; Terpene aldehydes

Indexed keywords

ALDEHYDE; ALPHA HYDROXY KETONE DERIVATIVE; ALPHA HYDROXYMETHYL KETONE; CAMPHANATE ESTER; COPPER DERIVATIVE; CYANOHYDRIN; ESTER; ISOPRENOID; KETONE; NITRILE; TERPENE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 3843092611     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200025618     Document Type: Article
Times cited : (3)

References (18)
  • 5
    • 0001537080 scopus 로고
    • Reactions of acyl anion equivalents derived from cyanohydrins, protected cyanohydrins and α-dialkylaminonitriles
    • Albright, J.D. Reactions of acyl anion equivalents derived from cyanohydrins, protected cyanohydrins and α-dialkylaminonitriles. Tetrahedron 1983, 39 (20), 3207-3233.
    • (1983) Tetrahedron , vol.39 , Issue.20 , pp. 3207-3233
    • Albright, J.D.1
  • 6
    • 0043206066 scopus 로고    scopus 로고
    • The role of 1,3-dithianes in natural product synthesis
    • Yus, M.; Najera, C.; Fonbelo, F. The role of 1,3-dithianes in natural product synthesis. Tetrahedron 2003, 59 (33), 6147-6212.
    • (2003) Tetrahedron , vol.59 , Issue.33 , pp. 6147-6212
    • Yus, M.1    Najera, C.2    Fonbelo, F.3
  • 7
    • 0001754157 scopus 로고
    • Forty years of umpolung in organometallic chemistry: From carbanionic nucleophiles to metallic electrophiles
    • Eisch, JJ. Forty years of umpolung in organometallic chemistry: from carbanionic nucleophiles to metallic electrophiles. J. Organomet. Chem. 1995, 5, 101-115.
    • (1995) J. Organomet. Chem. , vol.5 , pp. 101-115
    • Eisch, J.J.1
  • 8
    • 84970571837 scopus 로고
    • Applications of optically active aryl cyanohydrins in the synthesis of α-hydroxy aldehydes, α-hydroxy ketones and β-hydroxy amines
    • Jackson, W.R.; Jacobs, H.A.; Jayatilake, G.S.; Matthews, B.R.; Watson, K.G. Applications of optically active aryl cyanohydrins in the synthesis of α-hydroxy aldehydes, α-hydroxy ketones and β-hydroxy amines. Aust. J. Chem. 1990, 43, 2045-2062.
    • (1990) Aust. J. Chem. , vol.43 , pp. 2045-2062
    • Jackson, W.R.1    Jacobs, H.A.2    Jayatilake, G.S.3    Matthews, B.R.4    Watson, K.G.5
  • 9
    • 85064432185 scopus 로고
    • Catalytic asymmetric cyanohydrin synthesis
    • North, M. Catalytic asymmetric cyanohydrin synthesis. Synlett. 1993, 11, 807-820.
    • (1993) Synlett , vol.11 , pp. 807-820
    • North, M.1
  • 10
    • 0442310653 scopus 로고    scopus 로고
    • Pyruvate decarboxylase catalysed formation of terpenoid α-hydroxy ketones
    • Zorn, H.; Schüler, M.; Berger, R.G. Pyruvate decarboxylase catalysed formation of terpenoid α-hydroxy ketones. Biocatal. Biotransform. 2003, 21 (6), 341-347.
    • (2003) Biocatal. Biotransform. , vol.21 , Issue.6 , pp. 341-347
    • Zorn, H.1    Schüler, M.2    Berger, R.G.3
  • 11
    • 0041845348 scopus 로고    scopus 로고
    • Total chemical synthesis of 2-ethenyl-3,5-dimethylpyrazine and 3-ethenyl-2,5-dimethylpyrazine
    • Kurniadi, T.; Bel Rhlid, R.; Juillerat, M.-A.; Gefflaut, T.; Bolte, J.; Berger, R.G. Total chemical synthesis of 2-ethenyl-3,5-dimethylpyrazine and 3-ethenyl-2,5-dimethylpyrazine. Tetrahedron 2003, 59, 6109-6112.
    • (2003) Tetrahedron , vol.59 , pp. 6109-6112
    • Kurniadi, T.1    Bel Rhlid, R.2    Juillerat, M.-A.3    Gefflaut, T.4    Bolte, J.5    Berger, R.G.6
  • 12
    • 0001661818 scopus 로고
    • A facile synthesis of cyanohydrin trimethylsilyl ethers by the addition reaction of trimethylsilyl cyanide with aldehydes under basic conditions
    • Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. A facile synthesis of cyanohydrin trimethylsilyl ethers by the addition reaction of trimethylsilyl cyanide with aldehydes under basic conditions. Chem. Lett. 1991, 537-540.
    • (1991) Chem. Lett. , pp. 537-540
    • Kobayashi, S.1    Tsuchiya, Y.2    Mukaiyama, T.3
  • 13
    • 0000191820 scopus 로고
    • Tertiary carbinamines by addition of organocerium reagents to nitriles and ketimines
    • Ciganek, E. Tertiary carbinamines by addition of organocerium reagents to nitriles and ketimines. J. Org. Chem. 1992, 57 (16), 4521-4527.
    • (1992) J. Org. Chem. , vol.57 , Issue.16 , pp. 4521-4527
    • Ciganek, E.1
  • 14
    • 0000683791 scopus 로고
    • Copper(I)-activated addition of grignard reagents to nitriles. Synthesis of ketimines, ketones, and amines
    • Weiberth, F.; Hall, S.S. Copper(I)-activated addition of grignard reagents to nitriles. Synthesis of ketimines, ketones, and amines. J. Org. Chem. 1987, 52, 3901-3904.
    • (1987) J. Org. Chem. , vol.52 , pp. 3901-3904
    • Weiberth, F.1    Hall, S.S.2
  • 15
    • 0038556939 scopus 로고    scopus 로고
    • Réducion microbiologique de 3,4-dicétones et d'a-cétothioacétals
    • Bel Rhlid, R.; Renard, M.F.; Veschambre, H. Réducion microbiologique de 3,4-dicétones et d'a-cétothioacétals. Bull. Soc. Chim. Fr. 1996, 133(10), 1011-1022.
    • (1996) Bull. Soc. Chim. Fr. , vol.133 , Issue.10 , pp. 1011-1022
    • Bel Rhlid, R.1    Renard, M.F.2    Veschambre, H.3
  • 16
    • 0005408599 scopus 로고
    • Synthesis of enantiomerically pure forms of N-acyl derivatives of C-methyl analogs of the aminodeoxysugar L-acosamine from noncarbohydrate
    • Fonza, G.; Fuganti, C.; Graselli, P.; Mojori, L.; Pedrocchi-Fantoni, G.; Spreafico, F. Synthesis of enantiomerically pure forms of N-acyl derivatives of C-methyl analogs of the aminodeoxysugar L-acosamine from noncarbohydrate. J. Org. Chem. 1982, 47 (17), 3289-3296.
    • (1982) J. Org. Chem. , vol.47 , Issue.17 , pp. 3289-3296
    • Fonza, G.1    Fuganti, C.2    Graselli, P.3    Mojori, L.4    Pedrocchi-Fantoni, G.5    Spreafico, F.6
  • 17
    • 37049070595 scopus 로고
    • Decarboxylative incorporation of α-oxobutyrate and α-oxovalerate into (R)-α-hydroxyethyl- and n-propyl ketones on reaction with aromatic and α,β-unsaturated aldehydes in baker's yeast
    • Fuganti, C.; Graselli, P.; Poli, G.; Servi, S.; Zorzella, A. Decarboxylative incorporation of α-oxobutyrate and α-oxovalerate into (R)-α-hydroxyethyl- and n-propyl ketones on reaction with aromatic and α,β-unsaturated aldehydes in baker's yeast. J. Chem. Soc., Chem. Commun. 1988, 24, 1619-1621.
    • (1988) J. Chem. Soc., Chem. Commun. , vol.24 , pp. 1619-1621
    • Fuganti, C.1    Graselli, P.2    Poli, G.3    Servi, S.4    Zorzella, A.5
  • 18
    • 0028817159 scopus 로고
    • Linderanolides and iso-linderanolides, ten butanolides from Lindera glauca
    • Seki, K.; Sasaki, T.; Wano, S.; Haga, K.; Kaneko, R. Linderanolides and iso-linderanolides, ten butanolides from Lindera glauca. Phytochemistry 1995, 40(4), 1175-1182.
    • (1995) Phytochemistry , vol.40 , Issue.4 , pp. 1175-1182
    • Seki, K.1    Sasaki, T.2    Wano, S.3    Haga, K.4    Kaneko, R.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.