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Volumn 40, Issue 51, 1999, Pages 9077-9080

Reaction of dianions of acetoacetic esters with epibromohydrin derivatives: A novel synthesis of tetrahydrofuran derivatives and tetrahydropyran derivatives

Author keywords

Acetoacetic ester; Dianion; Epibromohydrin; Epoxide; Tetrahydrofuran; Tetrahydropyran

Indexed keywords

ACETOACETIC ACID DERIVATIVE; ANION; EPOXIDE; TETRAHYDROFURAN DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE;

EID: 0033579603     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01913-9     Document Type: Article
Times cited : (23)

References (29)
  • 9
    • 0002042832 scopus 로고
    • (b) Gosselck, J.; Winkler, A. Tetrahedron Lett. 1970, 2433-2436, 2437-2440. For a review of the dianion applied to the synthesis of β-lactams, see: Bose, A. K.; Manhas, M. S.; Chatterjee, B. G.; Abdulla, R. F. Synth. Commun. 1971, I, 51-73. For a list of examples, see: Larock, R. C. In Comprehensive Organic Transformations; VCH: New York, 1989; pp. 81, 83-84, 772-773.
    • (1970) Tetrahedron Lett. , pp. 2433-2436
    • Gosselck, J.1    Winkler, A.2
  • 10
    • 84963165831 scopus 로고
    • (b) Gosselck, J.; Winkler, A. Tetrahedron Lett. 1970, 2433-2436, 2437-2440. For a review of the dianion applied to the synthesis of β-lactams, see: Bose, A. K.; Manhas, M. S.; Chatterjee, B. G.; Abdulla, R. F. Synth. Commun. 1971, I, 51-73. For a list of examples, see: Larock, R. C. In Comprehensive Organic Transformations; VCH: New York, 1989; pp. 81, 83-84, 772-773.
    • (1971) Synth. Commun. , vol.1 , pp. 51-73
    • Bose, A.K.1    Manhas, M.S.2    Chatterjee, B.G.3    Abdulla, R.F.4
  • 11
    • 0003543593 scopus 로고
    • VCH: New York
    • (b) Gosselck, J.; Winkler, A. Tetrahedron Lett. 1970, 2433-2436, 2437-2440. For a review of the dianion applied to the synthesis of β-lactams, see: Bose, A. K.; Manhas, M. S.; Chatterjee, B. G.; Abdulla, R. F. Synth. Commun. 1971, I, 51-73. For a list of examples, see: Larock, R. C. In Comprehensive Organic Transformations; VCH: New York, 1989; pp. 81, 83-84, 772-773.
    • (1989) Comprehensive Organic Transformations , pp. 81
    • Larock, R.C.1
  • 12
    • 0032890262 scopus 로고    scopus 로고
    • While this study was being carried out, an interesting reaction of anion of ethyl -(triphenylphosphoranylidene)acetoacetate was reported. See: Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 153-156.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 153-156
    • Ceccarelli, S.1    Piarulli, U.2    Gennari, C.3
  • 13
    • 85038144892 scopus 로고    scopus 로고
    • note
    • 2, rt (ca. 40% overall yield).
  • 15
    • 0001109670 scopus 로고
    • The concentration of all the reactions in Table 1 was set to 0.1 M because the concentration of the reaction mixture also affects the ratio of 3U/3W. For the effect of the concentration on the ratio of 3U/3W, see: (a) Rhoads, S. J.; Holder, R. W. Tetrahedron 1969, 25, 5443-5450.
    • (1969) Tetrahedron , vol.25 , pp. 5443-5450
    • Rhoads, S.J.1    Holder, R.W.2
  • 17
    • 85038138880 scopus 로고    scopus 로고
    • note
    • 4, concentrated and dried under vacuum. Purification by silica gel chromatography (hexane:EtOAc 2:1) afforded 19.3 mg (32%) of 4a and 31.3 mg (52%) of 5a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.