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Volumn , Issue 9, 2006, Pages 2119-2133

Asymmetric dihydroxylation of β,γ-unsaturated carboxylic esters with trisubstituted C=C bonds - Enantioselective syntheses of trisubstituted γ-butyrolactones

Author keywords

, Unsaturated carboxylic esters; Asymmetric dihydroxylation; Butyrolactones; Stereoselective synthesis; Wolff rearrangement

Indexed keywords


EID: 33646388392     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200500963     Document Type: Article
Times cited : (44)

References (111)
  • 9
    • 4444295791 scopus 로고    scopus 로고
    • Recent syntheses of enantiomerically pure butanolides include the following: a) A. Samarat, H. Amri, Y. Landais, Tetrahedron 2004, 60, 8949-8956;
    • (2004) Tetrahedron , vol.60 , pp. 8949-8956
    • Samarat, A.1    Amri, H.2    Landais, Y.3
  • 27
    • 4544359033 scopus 로고    scopus 로고
    • 3-butenolides include the following: a) Y. Isemori, Y. Kobayashi, Synlett 2004, 11, 1941-1944;
    • (2004) Synlett , vol.11 , pp. 1941-1944
    • Isemori, Y.1    Kobayashi, Y.2
  • 36
    • 0000361656 scopus 로고
    • Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, Thieme, Stuttgart
    • d) G. Poli, C. Scolastico, Methoden Org. Chem. (Houben-Weyl) , 4th ed., 1952, Vol. E21e (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1995, pp. 4547-4598;
    • (1952) Methoden Org. Chem. (Houben-Weyl), 4th Ed. , vol.E21E , pp. 4547-4598
    • Poli, G.1    Scolastico, C.2
  • 38
    • 0000189702 scopus 로고    scopus 로고
    • Ed.: I. Ojima, Wiley-VCH, New York, Rationalizations of the absolute configuration of AD products
    • f) C. Bolm, J. P. Hildebrand, K. Muniz, Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, New York, 2000, 399-428. Rationalizations of the absolute configuration of AD products:
    • (2000) Catalytic Asymmetric Synthesis, 2nd Ed. , pp. 399-428
    • Bolm, C.1    Hildebrand, J.P.2    Muniz, K.3
  • 41
    • 33646387102 scopus 로고    scopus 로고
    • [6];
    • [6];
  • 42
    • 33646396391 scopus 로고    scopus 로고
    • [6]
    • [6]
  • 44
    • 33646388584 scopus 로고    scopus 로고
    • [6]
    • [6]
  • 49
    • 0002860538 scopus 로고
    • Arndt-Eistert homologation review: a) W. E. Bachmann, W. S. Struve, Org. React. 1942, 1, 38-62. Arndt-Eistert homologation of α,β-unsaturated acid chlorides:
    • (1942) Org. React. , vol.1 , pp. 38-62
    • Bachmann, W.E.1    Struve, W.S.2
  • 50
    • 15944365284 scopus 로고
    • b) J. A. Moore, J. Org. Chem. 1955, 20, 1607-1612. Syntheses of α,β-unsaturated diazo ketones from α,β-unsaturated acid chlorides (without ensuing Wolff rearrangement):
    • (1955) J. Org. Chem. , vol.20 , pp. 1607-1612
    • Moore, J.A.1
  • 57
    • 33646404251 scopus 로고    scopus 로고
    • [8]
    • [8]
  • 58
    • 33646397228 scopus 로고    scopus 로고
    • [10b]
    • [10b];
  • 70
    • 0000103923 scopus 로고
    • L. A. Paquette (Editor-in-Chief), John Wiley & Sons, Sussex, England
    • L. A. Paquette (Editor-in-Chief), Encyclopedia of Reagents for Organic Synthesis, vol. 7, John Wiley & Sons, Sussex, England, 1995, 5248-5251;
    • (1995) Encyclopedia of Reagents for Organic Synthesis , vol.7 , pp. 5248-5251
  • 75
    • 33646421568 scopus 로고    scopus 로고
    • Dissertation, University of Freiburg
    • synthesis of ethyl ester analogue of 24: S. Anklam, Dissertation, University of Freiburg, 2003, pp. 185-186.
    • (2003) , pp. 185-186
    • Anklam, S.1
  • 76
    • 33646434721 scopus 로고    scopus 로고
    • Dissertation, University of Freiburg
    • Syntheses of compounds 23 and 25: S. Braukmüller, Dissertation, University of Freiburg, 2002, pp. 166-167.
    • (2002) , pp. 166-167
    • Braukmüller, S.1
  • 77
    • 0010402752 scopus 로고
    • Syntheses of reagent 21 described, inter alia, by: D. E. McGreer, N. W. K. Chiu, Can. J. Chem. 1968, 46, 2225-2232;
    • (1968) Can. J. Chem. , vol.46 , pp. 2225-2232
    • McGreer, D.E.1    Chiu, N.W.K.2
  • 79
    • 33646419462 scopus 로고    scopus 로고
    • Dissertation, University of Freiburg
    • Phosphonate 38 was kindly supplied by Tom Olpp (preparation: T. Olpp, Dissertation, University of Freiburg, 2005, pp. 281-282).
    • (2005) , pp. 281-282
    • Olpp, T.1
  • 80
    • 0029052069 scopus 로고
    • Different p,p-(Aryloxy)-substituted HWE reagents are known to form α,β-unsaturated esters (Z)-selectively from studies by Ando etal.: a) K. Ando, Tetrahedron Lett. 1995, 36, 4105-4108;
    • (1995) Tetrahedron Lett. , vol.36 , pp. 4105-4108
    • Ando, K.1
  • 81
    • 0000262852 scopus 로고    scopus 로고
    • b) K. Ando, J. Org. Chem. 1997, 62, 1934-1939;
    • (1997) J. Org. Chem. , vol.62 , pp. 1934-1939
    • Ando, K.1
  • 82
    • 0032514965 scopus 로고    scopus 로고
    • c) K. Ando, J. Org. Chem. 1998, 63, 8411-8416;
    • (1998) J. Org. Chem. , vol.63 , pp. 8411-8416
    • Ando, K.1
  • 83
    • 0033615594 scopus 로고    scopus 로고
    • d) K. Ando, J. Org. Chem. 1999, 64, 8406-8408;
    • (1999) J. Org. Chem. , vol.64 , pp. 8406-8408
    • Ando, K.1
  • 85
    • 0034903277 scopus 로고    scopus 로고
    • f) K. Ando, Synlett 2001, 1272-1274.
    • (2001) Synlett , pp. 1272-1274
    • Ando, K.1
  • 89
    • 0000814530 scopus 로고
    • Glycol Cleavage Reactions
    • Eds.: B. M. Trost, I. Fleming, Pergamon Press, Oxford
    • Reviews: a) T. K. M. Shing, "Glycol Cleavage Reactions", in: Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), 7, 703-716, Pergamon Press, Oxford, 1991;
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 703-716
    • Shing, T.K.M.1
  • 98
    • 0002998997 scopus 로고
    • Compound 4a was described previously by: R. C. Larock, J. Org. Chem. 1975, 40, 3237-3242.
    • (1975) J. Org. Chem. , vol.40 , pp. 3237-3242
    • Larock, R.C.1
  • 101
    • 84981759899 scopus 로고
    • This ylide was prepared by a procedure analogous to that described by: H.-J. Bestmann, H. Hartung, Chem. Ber. 1966, 99, 1198-1207.
    • (1966) Chem. Ber. , vol.99 , pp. 1198-1207
    • Bestmann, H.-J.1    Hartung, H.2
  • 109
    • 0038057688 scopus 로고    scopus 로고
    • Compound (Z)-33 was described previously by: Y. Shen, Y. Zhang, Heteroat. Chem. 2003, 14, 276-279.
    • (2003) Heteroat. Chem. , vol.14 , pp. 276-279
    • Shen, Y.1    Zhang, Y.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.