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Volumn 9, Issue 4, 1998, Pages 381-387

Facile palladium-mediated conversion of ethanethiol esters to aldehydes and ketones

Author keywords

Aldehyde; Ketone; Organozinc reagent; Palladium catalyst; Thiol ester; Trietyl silane

Indexed keywords


EID: 0032332565     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0103-50531998000400011     Document Type: Article
Times cited : (64)

References (24)
  • 1
    • 0001582732 scopus 로고
    • For representative examples, see: (a) Cha, J.S.; Kim, J.E.; Yoon, M.S.; Kim, Y.S. Tetrahedron Lett. 1987, 28, 6231. (b) Corriu, R.J.P.; Lanneau, G.F.; Perrot, M. Tetrahedron Lett. 1987, 28, 3941. (c) Brown, H.C.; Cha, J.S.; Nazer, B.; Yoon, N.M. J. Am. Chem. Soc. 1984, 106, 8001 and references sited therein.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 6231
    • Cha, J.S.1    Kim, J.E.2    Yoon, M.S.3    Kim, Y.S.4
  • 2
    • 0001644987 scopus 로고
    • For representative examples, see: (a) Cha, J.S.; Kim, J.E.; Yoon, M.S.; Kim, Y.S. Tetrahedron Lett. 1987, 28, 6231. (b) Corriu, R.J.P.; Lanneau, G.F.; Perrot, M. Tetrahedron Lett. 1987, 28, 3941. (c) Brown, H.C.; Cha, J.S.; Nazer, B.; Yoon, N.M. J. Am. Chem. Soc. 1984, 106, 8001 and references sited therein.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 3941
    • Corriu, R.J.P.1    Lanneau, G.F.2    Perrot, M.3
  • 3
    • 0000887714 scopus 로고
    • and references sited therein
    • For representative examples, see: (a) Cha, J.S.; Kim, J.E.; Yoon, M.S.; Kim, Y.S. Tetrahedron Lett. 1987, 28, 6231. (b) Corriu, R.J.P.; Lanneau, G.F.; Perrot, M. Tetrahedron Lett. 1987, 28, 3941. (c) Brown, H.C.; Cha, J.S.; Nazer, B.; Yoon, N.M. J. Am. Chem. Soc. 1984, 106, 8001 and references sited therein.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 8001
    • Brown, H.C.1    Cha, J.S.2    Nazer, B.3    Yoon, N.M.4
  • 4
    • 0001545278 scopus 로고
    • Nucleophilic Addition to Carboxylic Acid Derivatives
    • Trost, B.M.; Fleming, I., Eds.; Pergamon: Oxford, Chapter 1.13
    • (a) For general reviews for conversion of carboxylic acid into ketones, see: O'Neill, B.T. "Nucleophilic Addition to Carboxylic Acid Derivatives", In Comprehensive Organic Synthesis.; Trost, B.M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, Chapter 1.13, p 397.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 397
    • O'Neill, B.T.1
  • 6
    • 0002471288 scopus 로고
    • 2-catalyzed ketone formation from S-(2-pyridyl) thioates in the presence of Zn and alkyl iodide: Onaka, M.; Matsuoka, Y.; Mukaiyama, T. Chem. Lett. 1981, 531.
    • (1981) Chem. Lett. , pp. 531
    • Onaka, M.1    Matsuoka, Y.2    Mukaiyama, T.3
  • 8
    • 0025073031 scopus 로고
    • (a) For the preliminary report on the reduction of ethanethiol esters to aldehydes, see: Fukuyama, T.; Lin, S.-C.; Li, L. J. Am. Chem. Soc. 1990, 112, 7050.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 7050
    • Fukuyama, T.1    Lin, S.-C.2    Li, L.3
  • 16
    • 4243489506 scopus 로고
    • and references cited therein
    • (a) For a general review of preparation of organozinc reagents, see: Knochel, P.; Singer, R.D. Chem. Rev. 1993, 93, 2117, and references cited therein.
    • (1993) Chem. Rev. , vol.93 , pp. 2117
    • Knochel, P.1    Singer, R.D.2
  • 23
    • 3042946455 scopus 로고    scopus 로고
    • note
    • HPLC analysis was performed with a chiral HPLC column using a racemic mixture as references (DAICEL Chiralcel-OD, 4.6 mm I.D. × 250 mm, 95/5 n-hexane/2-propanol, 1.0 mL/min, 40°C).
  • 24
    • 3042882906 scopus 로고    scopus 로고
    • note
    • The thiol ester was prepared from N-Cbz-L-phenylalanine via mixed anhydride.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.