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Volumn 43, Issue 1, 2010, Pages 3-12

Powerful and versatile silicon lewis acids for asymmetric chemical synthesis

Author keywords

Allylsilane; Asymmetric synthesis; Chiral carbinamines; Silicon lewis acid; Strained silacycles

Indexed keywords


EID: 77953878892     PISSN: 00025100     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (31)

References (70)
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    • Two groups had reported the use of tartrate-ester-derived allyl(chloro)dioxasilacyclopentanes in uncatalyzed aldehyde allylation reactions. In both cases, the reactivity was attributed to the binding of a Lewis base, while ring strain was not mentioned in either report
    • Two groups had reported the use of tartrate-ester-derived allyl(chloro)dioxasilacyclopentanes in uncatalyzed aldehyde allylation reactions. In both cases, the reactivity was attributed to the binding of a Lewis base, while ring strain was not mentioned in either report: Wang, Z.; Wang, D.; Sui, X. Chem. Commun. 1996, 2261.
    • (1996) Chem. Commun , pp. 2261
    • Wang, Z.1    Wang, D.2    Sui, X.3
  • 23
    • 0035803698 scopus 로고    scopus 로고
    • For other reports of asymmetric allylation of acylhydrazones, see
    • For other reports of asymmetric allylation of acylhydrazones, see: Friestad, G. K.; Ding, H. Angew. Chem., Int. Ed. 2001, 40, 4491.
    • (2001) Angew. Chem., Int. Ed , vol.40 , pp. 4491
    • Friestad, G.K.1    Ding, H.2
  • 33
    • 13744258949 scopus 로고    scopus 로고
    • For a theoretical analysis of the origins of enantioselectivity in this aldehyde allylation reaction, see
    • For a theoretical analysis of the origins of enantioselectivity in this aldehyde allylation reaction, see Zhang, X.; Houk, K. N.; Leighton, J. L. Angew. Chem., Int. Ed. 2005, 44, 938.
    • (2005) Angew. Chem., Int. Ed , vol.44 , pp. 938
    • Zhang, X.1    Houk, K.N.2    Leighton, J.L.3
  • 42
    • 0041910844 scopus 로고    scopus 로고
    • Kobayashi had previously made a similar analogy between acylhydrazones and 2-aminophenol-derived imines for imine allylation with allyltrichlorosilane. See
    • Kobayashi had previously made a similar analogy between acylhydrazones and 2-aminophenol-derived imines for imine allylation with allyltrichlorosilane. See Sugiura, M.; Robvieux, F.; Kobayashi, S. Synlett 2003, 1749.
    • (2003) Synlett , pp. 1749
    • Sugiura, M.1    Robvieux, F.2    Kobayashi, S.3
  • 47
    • 0036495555 scopus 로고    scopus 로고
    • Cross-metathesis reactions between allylboranes and various alkenes in the context of aldehyde allylboration reactions have been demonstrated. See
    • Cross-metathesis reactions between allylboranes and various alkenes in the context of aldehyde allylboration reactions have been demonstrated. See: Goldberg, S. D.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 807.
    • (2002) Angew. Chem., Int. Ed , vol.41 , pp. 807
    • Goldberg, S.D.1    Grubbs, R.H.2
  • 50
    • 33846906752 scopus 로고    scopus 로고
    • For two recent reviews that cover Friedel-Crafts alkylations with imines, see
    • For two recent reviews that cover Friedel-Crafts alkylations with imines, see: Friestad, G. K.; Mathies, A. K. Tetrahedron 2007, 63, 2541.
    • (2007) Tetrahedron , vol.63 , pp. 2541
    • Friestad, G.K.1    Mathies, A.K.2
  • 53
    • 0037146071 scopus 로고    scopus 로고
    • For chiral Lewis acid catalyzed cycloaddition reactions between acylhydrazones and enol ethers, see
    • For chiral Lewis acid catalyzed cycloaddition reactions between acylhydrazones and enol ethers, see: Kobayashi, S.; Shimizu, H.; Yamashita, Y.; Ishitani, H.; Kobayashi, J. J. Am. Chem. Soc. 2002, 124, 13678.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 13678
    • Kobayashi, S.1    Shimizu, H.2    Yamashita, Y.3    Ishitani, H.4    Kobayashi, J.5
  • 55
    • 0033516315 scopus 로고    scopus 로고
    • For the chiral Lewis acid catalyzed addition of diazo esters to imines, see
    • For the chiral Lewis acid catalyzed addition of diazo esters to imines, see: Antilla, J. C.; Wulff, W. D. J. Am. Chem. Soc. 1999, 121, 5099.
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 5099
    • Antilla, J.C.1    Wulff, W.D.2
  • 59
    • 55549092803 scopus 로고    scopus 로고
    • For the chiral Brønsted acid catalyzed addition of diazo amides to imines, see
    • For the chiral Brønsted acid catalyzed addition of diazo amides to imines, see Hashimoto, T.; Uchiyama, N.; Maruoka, K. J. Am. Chem. Soc. 2008, 130, 14380.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 14380
    • Hashimoto, T.1    Uchiyama, N.2    Maruoka, K.3
  • 68
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    • For enantioselective Pictet-Spengler reactions with ketimine substrates, see
    • For enantioselective Pictet-Spengler reactions with ketimine substrates, see: Raheem, I. T.; Thiara, P. S.; Peterson, E. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 13404.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 13404
    • Raheem, I.T.1    Thiara, P.S.2    Peterson, E.A.3    Jacobsen, E.N.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.