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Volumn 16, Issue 18, 2010, Pages 5443-5453

Abnormal behaviour of allenylsulfones under Lu's reaction conditions: Synthesis of enantiopure polyfunctionalised cyclopentenes

Author keywords

Asymmetric synthesis; Cycloaddition; Lactones; Polycycles

Indexed keywords

ASYMMETRIC SYNTHESIS; COMPLETE CONTROL; CYCLOADDITIONS; CYCLOPENTENES; DIFFERENT MECHANISMS; ENANTIOPURE; FACIAL SELECTIVITY; FURANONES; GOOD YIELD; POLYCYCLES; REACTION CONDITIONS; STEREOCHEMICAL CONTROL; SULFINYL GROUP; SULFONYL GROUPS;

EID: 77951966638     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903185     Document Type: Article
Times cited : (35)

References (73)
  • 5
    • 38949177006 scopus 로고    scopus 로고
    • references therein
    • G. S. Creech, O. Kwon, Org. Lett. 2008, 10, 429-432, and references therein.
    • (2008) Org. Lett. , vol.10 , pp. 429-432
    • Creech, G.S.1    Kwon, O.2
  • 7
    • 33745941049 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 1426-1429.
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 1426-1429
  • 8
    • 77951968915 scopus 로고    scopus 로고
    • For acyclic two-carbon components, see: a references [2] and [5]
    • For acyclic two-carbon components, see: a) references [2] and [5];
  • 13
    • 0037073879 scopus 로고    scopus 로고
    • For cyclic two-carbon components, see: a) references [5] and [6d]; b) Y. Du, X. Lu, Y. Yu, J. Org. Chem. 2002, 67, 8901.-8905;
    • (2002) J. Org. Chem. , vol.67 , pp. 8901-8905
    • Du, Y.1    Lu, X.2    Yu, Y.3
  • 17
    • 77951957382 scopus 로고    scopus 로고
    • for use of chiral phosphines
    • b) for use of chiral phosphines,
  • 25
    • 77951959477 scopus 로고    scopus 로고
    • Ph.D. Thesis, Universidad Autónoma de Madrid (Spain)
    • b) A. Fraile, Ph.D. Thesis, Universidad Autónoma de Madrid (Spain), 2003.
    • (2003)
    • Fraile, A.1
  • 38
    • 64249161117 scopus 로고    scopus 로고
    • references therein
    • Z-X. Yu, and co-workers suggest the intervention of water molecules to explain the intramolecular [l,2]-proton shift indicated in Scheme 1, see: Y. Liang, S. Liu, Z-X. Yu, Synlett 2009, 905-909, and references therein.
    • (2009) Synlett , pp. 905-909
    • Liang, Y.1    Liu, S.2    Yu, Z.-X.3
  • 39
    • 53749090597 scopus 로고    scopus 로고
    • [7c] and allenyl phosphates (A. Panossian, N. Fleury-Bregeot, A. Marinetti, Eur. J. Org. Chem. 2008, 3826-3833) have been studied as precursors of the three-carbon fragment in these asymmetric [3+2] cycloadditions catalysed by phosphines.
    • (2008) Eur. J. Org. Chem. , pp. 3826-3833
    • Panossian, A.1    Fleury-Bregeot, N.2    Marinetti, A.3
  • 41
    • 84949802859 scopus 로고    scopus 로고
    • The Chemistry of Sulphones and Sulphoxides (Eds.: S. Patai, Z. Rappoport, C. Stirling), Wiley, New York, 1988
    • a) The Chemistry of Sulphones and Sulphoxides (Eds.: S. Patai, Z. Rappoport, C. Stirling), Wiley, New York, 1988;
  • 56
    • 77951948953 scopus 로고    scopus 로고
    • The low yield obtained from reaction of 2b, compared with that obtained from 2 a, could be a consequence of the lower stability of substrate 2b and adduct 8b in relation to the corresponding a isomers, under the reaction conditions
    • The low yield obtained from reaction of 2b, compared with that obtained from 2 a, could be a consequence of the lower stability of substrate 2b and adduct 8b in relation to the corresponding a isomers, under the reaction conditions.
  • 57
    • 77951951981 scopus 로고    scopus 로고
    • note
    • 2Ph) was similar to that of the starting allene/sulfinate ratio.
  • 59
    • 77951946372 scopus 로고    scopus 로고
    • 3 and water) to those used for Lu's reactions (under these conditions only traces of cyclopentenes are obtained), which determine a different reaction course
    • 3 and water) to those used for Lu's reactions (under these conditions only traces of cyclopentenes are obtained), which determine a different reaction course.
  • 60
    • 60949108432 scopus 로고    scopus 로고
    • For other reactions of a-methyl allenoates with electron-deficient olefins catalysed by tetra-n-butylammonium fluoride (to afford 2-alkynyl-2-substituted glutaric acid derivatives), see: L.-P. Liu, B. Xu, G. B. Hammond, Org. Lett. 2008, 10, 3887-3890.
    • (2008) Org. Lett. , vol.10 , pp. 3887-3890
    • Liu, L.-P.1    Xu, B.2    Hammond, G.B.3
  • 61
    • 77951969975 scopus 로고    scopus 로고
    • The ee values were determined by HPLC employing a Daicel Chiralpack AD column, with hexane and isopropyl alcohol as the eluents
    • The ee values were determined by HPLC employing a Daicel Chiralpack AD column, with hexane and isopropyl alcohol as the eluents.
  • 62
    • 77951961720 scopus 로고    scopus 로고
    • Although no adducts of 2 b with alienes 4 and 5 were obtained, the enantiomers of 13a and 14a could be accessible by this route
    • Although no adducts of 2 b with alienes 4 and 5 were obtained, the enantiomers of 13a and 14a could be accessible by this route.
  • 63
    • 77951955452 scopus 로고    scopus 로고
    • note
    • Preliminary studies of these reactions have been performed. Reaction of racemic (±)-6 with diethyl malonate only provides one diastereoisomer, which results from the approach of the nucleophile to the convex face of the bicyclic system. The application of these products to the synthesis of a range of known and novel structures is under investigation.
  • 66
    • 2442609914 scopus 로고    scopus 로고
    • For the use of 2-formylcyclopentanecarboxylates derivatives in the asymmetric synthesis of antibiotic, antiviral, and antitumoural (+)brefeldin A, see: a) B. M, Trost, M . L. Crawley, Chem. Eur. J 2004, 10, 2237-2252;
    • (2004) Chem. Eur. J , vol.10 , pp. 2237-2252
    • Trost, B.M.1    Crawley, M.L.2
  • 69
    • 42149126132 scopus 로고    scopus 로고
    • For recent use of cyclopentanecarbaldehydes, see: a) S. Forster, G. Heimchen, Synlett 2008, 831-836;
    • (2008) Synlett , pp. 831-836
    • Forster, S.1    Heimchen, G.2
  • 73
    • 77951963802 scopus 로고    scopus 로고
    • CCDC-755291 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC-755291 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data-request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.