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Volumn 36, Issue 5, 1997, Pages 518-521

Asymmetric Heck Reactions via Neutral Intermediates: Enhanced Enantioselectivity with Halide Additives Gives Mechanistic Insights

Author keywords

Asymmetric catalysis; Asymmetric synthesis; Heck reactions; Palladium

Indexed keywords


EID: 0030902183     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199705181     Document Type: Article
Times cited : (112)

References (43)
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    • f) ref. [2].
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    • Notable exception: O. Loiseleur, P. Meier, A. Pfaltz, Angew. Chem. 1996, 108, 218; Angew. Chem. Int. Ed. Engl. 1996, 35, 200.
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    • b) incisive recent studies: J. M. Brown, J. J. Pérez-Torrente, N. W. Alcock, H. J. Clase, Organometallics 1995, 14, 207; J. M. Brown, K. K. M. Hii, Angew. Chem. 1996, 108, 679; Angew. Chem. Int. Ed. Engl. 1996, 35, 657.
    • (1996) Angew. Chem. , vol.108 , pp. 679
    • Brown, J.M.1    Hii, K.K.M.2
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    • 33748725061 scopus 로고    scopus 로고
    • b) incisive recent studies: J. M. Brown, J. J. Pérez-Torrente, N. W. Alcock, H. J. Clase, Organometallics 1995, 14, 207; J. M. Brown, K. K. M. Hii, Angew. Chem. 1996, 108, 679; Angew. Chem. Int. Ed. Engl. 1996, 35, 657.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 657
  • 25
    • 85033147279 scopus 로고    scopus 로고
    • The other five-coordinate intermediates that would intervene in the insertion process are not shown in Scheme 1 [12]
    • The other five-coordinate intermediates that would intervene in the insertion process are not shown in Scheme 1 [12].
  • 27
    • 85033134891 scopus 로고    scopus 로고
    • note
    • -1).
  • 28
    • 85033139460 scopus 로고    scopus 로고
    • A Diacel Chiralpak AS or OB-H: column was employed: precision in measuring ee is ±2%
    • A Diacel Chiralpak AS or OB-H: column was employed: precision in measuring ee is ±2%.
  • 30
    • 0000172384 scopus 로고    scopus 로고
    • ref. [10a]
    • - : a) A. Jutand, A. Mosleh, Organometallics, 1995, 14, 1810; b) ref. [10a].
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    • 4
    • 4.
  • 36
    • 85033131283 scopus 로고    scopus 로고
    • note
    • [22] for brevity these intermediates are not shown in Scheme 1.
  • 37
    • 0001291247 scopus 로고
    • Substitution reactions of 16e square-planar complexes are typically associative: R. J. Cross, Adv. Inorg. Chem. 1989, 34, 219.
    • (1989) Adv. Inorg. Chem. , vol.34 , pp. 219
    • Cross, R.J.1
  • 39
    • 0347914999 scopus 로고
    • This step could be either the formation of a pentacoordinate intermediate from 5 or the evolution of a pentacoordinate intermediate to 7. The first irreversible enantiodifferentiating step would determine asymmetric induction: C. R. Landis, J. Halpern, J. Am. Chem. Soc. 1987, 109, 425.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 425
    • Landis, C.R.1    Halpern, J.2
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    • 33-allylpalladium carbanion trapping reaction resulted in moderate increases in enantioselectivity that were ascribed to complexation with the sodium enolate.
    • (1988) J. Org. Chem. , vol.53 , pp. 2112
    • Andersson, C.M.1    Hallberg, A.2
  • 43
    • 85033155353 scopus 로고    scopus 로고
    • note
    • 33-allylpalladium carbanion trapping reaction resulted in moderate increases in enantioselectivity that were ascribed to complexation with the sodium enolate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.