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Volumn 68, Issue 7, 2003, Pages 2779-2789

A new synthesis and stereocontrolled functionalization of substituted silacyclopent-3-enes

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; HYDROXYLATION; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 0037419459     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026774a     Document Type: Article
Times cited : (28)

References (62)
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    • For a recent functionalization of the parent unsubstituted silacyclopent-3-ene 1, see: a) Liu, D.; Kozmin, S. A. Org. Lett. 2002, 4, 3005-3007. b) Liu, D.; Kozmin, S. A. Angew. Chem., Int. Ed. 2001, 40, 4757-4759.
    • (2002) Org. Lett. , vol.4 , pp. 3005-3007
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  • 3
    • 0035905364 scopus 로고    scopus 로고
    • For a recent functionalization of the parent unsubstituted silacyclopent-3-ene 1, see: a) Liu, D.; Kozmin, S. A. Org. Lett. 2002, 4, 3005-3007. b) Liu, D.; Kozmin, S. A. Angew. Chem., Int. Ed. 2001, 40, 4757-4759.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 4757-4759
    • Liu, D.1    Kozmin, S.A.2
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    • and references therein
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  • 17
    • 0032580376 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see: a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
    • (1998) Tetrahedron , vol.54 , pp. 4413-4450
    • Grubbs, R.H.1    Chang, S.2
  • 18
    • 28244440935 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see: a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
    • (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 371-388
    • Armstrong, S.K.1
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    • 0030771019 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see: a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450. b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388. c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 2036-2056
    • Schuster, M.1    Blechert, S.2
  • 20
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    • 9 is commercially available. For a synthesis, see: Nasiak, L. D.; Post, H. W. J. Org. Chem. 1959, 24, 489-492.
    • (1959) J. Org. Chem. , vol.24 , pp. 489-492
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  • 34
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    • note
    • Direct coupling of the allyllithium species with aldehydes led exclusively to the γ-product.
  • 35
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    • note
    • 2 for 3-18 h at rt to afford 15a-c in 74%, 79%, and 81% yield, respectively.
  • 36
    • 0242391632 scopus 로고    scopus 로고
    • note
    • 2 under reflux.
  • 37
    • 0000652169 scopus 로고
    • The synthesis of nonsubstituted 1-silacyclopent-3-enes 1 through RCM using a tungsten catalyst has been reported. Poor to excellent results (8-90% yield) were obtained depending on the nature of the substituents at the silicon center. See: a) Leconte, M.; Pagano, S.; Mutch, A.; Lefebvre, F.; Basset, J. M. Bull. Soc. Chim. Fr. 1995, 132, 1069-1071. b) Ahmad, I.; Falck-Pedersen, M. L.; Undheim, K. J. Organomet. Chem. 2001, 625, 160-172.
    • (1995) Bull. Soc. Chim. Fr. , vol.132 , pp. 1069-1071
    • Leconte, M.1    Pagano, S.2    Mutch, A.3    Lefebvre, F.4    Basset, J.M.5
  • 38
    • 0035932792 scopus 로고    scopus 로고
    • The synthesis of nonsubstituted 1-silacyclopent-3-enes 1 through RCM using a tungsten catalyst has been reported. Poor to excellent results (8-90% yield) were obtained depending on the nature of the substituents at the silicon center. See: a) Leconte, M.; Pagano, S.; Mutch, A.; Lefebvre, F.; Basset, J. M. Bull. Soc. Chim. Fr. 1995, 132, 1069-1071. b) Ahmad, I.; Falck-Pedersen, M. L.; Undheim, K. J. Organomet. Chem. 2001, 625, 160-172.
    • (2001) J. Organomet. Chem. , vol.625 , pp. 160-172
    • Ahmad, I.1    Falck-Pedersen, M.L.2    Undheim, K.3
  • 39
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    • note
    • 6
  • 43
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    • note
    • All attempts to separate the mixture of diastereomers by chromatography through silica gel led to decomposition.
  • 54
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    • Theoretical studies have shown that in allylsilanes, groundstate interactions between alkene π-orbital and the coplanar C-Si bond raises the HOMO of the allylsilane and thus make it more reactive towards electrophiles, see: Kahn, S. D.; Pau, C. F.; Chamberlin, A. R.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 650-663.
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    • Kahn, S.D.1    Pau, C.F.2    Chamberlin, A.R.3    Hehre, W.J.4
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    • (1996) Advances in Silicon Chemistry , vol.3 , pp. 1
    • Tamao, K.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.