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Volumn 7, Issue 5, 2001, Pages 1056-1068

C-C versus C-O anionic domino cycloalkylation of stabilized carbanions: Facile one-pot stereoselective preparation of functionalized bridged bicycloalkanones and cyclic enol ethers

Author keywords

Carbanions; Cycloalkylation; Domino reactions; Enols

Indexed keywords

ALKYLATION; ETHERS; ISOMERS; KETONES; NEGATIVE IONS;

EID: 0035793827     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010302)7:5<1056::AID-CHEM1056>3.0.CO;2-D     Document Type: Article
Times cited : (26)

References (99)
  • 2
    • 0002782655 scopus 로고
    • (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford
    • D. Caine in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 1;
    • (1991) Comprehensive Organic Synthesis, Vol. 3 , vol.3 , pp. 1
    • Caine, D.1
  • 11
    • 0028258690 scopus 로고
    • For a study on the related α,α′-dialkylation of unfunctionalized cyclic and acyclic ketones or using β-ketophosphonates, see: R. B. Bates, S. R. Taylor, J. Org. Chem. 1994, 59, 245;
    • (1994) J. Org. Chem. , vol.59 , pp. 245
    • Bates, R.B.1    Taylor, S.R.2
  • 27
    • 0347492491 scopus 로고
    • For preliminary results on the selective C-C dialkylation of 1,3-diactivated cyclopentanone, see: T. Lavoisier, J. Rodriguez, Synlett 1995, 1241.
    • (1995) Synlett , pp. 1241
    • Lavoisier, T.1    Rodriguez, J.2
  • 31
    • 0002631382 scopus 로고    scopus 로고
    • For preliminary results on the selective C-O cycloalkylation of cyclic and acyclic 1,3-diactivated ketones, see: a) T. Lavoisier, J. Rodriguez, Synlett 1996, 339.
    • (1996) Synlett , pp. 339
    • Lavoisier, T.1    Rodriguez, J.2
  • 32
    • 0001075622 scopus 로고
    • While this work was underway a similar approach concerning the reactivity of α-substituted cyclohexanone anions with cis- or trans-1,4-dibromo-2-butene has been reported: b) T. Wang, J. Chen, K. Zhao, J. Org. Chem. 1995, 60, 2668.
    • (1995) J. Org. Chem. , vol.60 , pp. 2668
    • Wang, T.1    Chen, J.2    Zhao, K.3
  • 39
    • 0001866893 scopus 로고    scopus 로고
    • For a recent review on the synthesis and reactivity of bicyclo[3.2.1]octanes, see: M.-H. Filippini, J. Rodriguez, Chem. Rev. 1999, 1, 27.
    • (1999) Chem. Rev. , vol.1 , pp. 27
    • Filippini, M.-H.1    Rodriguez, J.2
  • 42
    • 0001704637 scopus 로고
    • For other synthetic transformations involving 1,2-bis(methylene)cycloalkanes, see: R. D. Rieke, H. Xiong, J. Org. Chem. 1992, 57, 6560;
    • (1992) J. Org. Chem. , vol.57 , pp. 6560
    • Rieke, R.D.1    Xiong, H.2
  • 53
    • 0030926915 scopus 로고    scopus 로고
    • For recent applications of this approach for the construction of hydrofurans, see for example: T. Lavoisier-Gallo, J. Rodriguez, J. Org. Chem. 1997, 62, 3787;
    • (1997) J. Org. Chem. , vol.62 , pp. 3787
    • Lavoisier-Gallo, T.1    Rodriguez, J.2
  • 65
    • 15844366864 scopus 로고
    • For a review on synthetic routes to tetrahydrofurans, see: T. L. B. Boivin, Tetrahedron 1987, 43, 3309.
    • (1987) Tetrahedron , vol.43 , pp. 3309
    • Boivin, T.L.B.1
  • 66
    • 0029915916 scopus 로고    scopus 로고
    • For some recent synthetic applications of related functionalized tetrahydrofurans, see for example: V. Dalla, P. Pale, Tetrahedron Lett. 1996, 37, 2777;
    • (1996) Tetrahedron Lett. , vol.37 , pp. 2777
    • Dalla, V.1    Pale, P.2
  • 75
    • 85027999108 scopus 로고    scopus 로고
    • See also ref. [29]. For the selective C-C cycloalkylation of dimethyl malonate with (Z)-1,4-dichloro-2-butene, see: J.-P. Deprés, A. E. Greene, Org. Synth. 1997, 75, 195.
    • (1997) Org. Synth. , vol.75 , pp. 195
    • Deprés, J.-P.1    Greene, A.E.2
  • 79
    • 0005589818 scopus 로고
    • For preferred trans alkylation of related endocyclic enolates with an asymmetric center at the β-position, see: N. Ouvrard, J. Rodriguez, M. Santelli, Angew. Chem. 1992, 104, 1658;
    • (1992) Angew. Chem. , vol.104 , pp. 1658
    • Ouvrard, N.1    Rodriguez, J.2    Santelli, M.3
  • 82
    • 0005607819 scopus 로고    scopus 로고
    • note
    • The SMx solvatation models found in AMPAC were contributed from the University of Minnesota by G. D. Hawkins, D. A. Liotard, C. J. Cameron and D. G. Truhlar.
  • 84
    • 0005623587 scopus 로고    scopus 로고
    • note
    • AM1 calculations do not offer the possibility to modelize the influence of the potassium cation. Although highly time consuming and therefore beyond our possibilities, ab initio calculations might provide a better quantification of the observed selectivity of the reaction.
  • 86
    • 33847574575 scopus 로고    scopus 로고
    • Calculations were performed with the AMPAC 6.56, Semichem, Shawnes, KS 66216, USA
    • Calculations were performed with the AMPAC 6.56, Semichem, Shawnes, KS 66216, USA.
  • 87
    • 0004133516 scopus 로고    scopus 로고
    • Gaussian, Inc., Pittsburgh, PA
    • Gaussian 98, Revision A.7, Gaussian, Inc., Pittsburgh, PA, 1998.
    • (1998) Gaussian 98, Revision A.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.