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Volumn 46, Issue 9, 2007, Pages 1485-1488

Stereochemical and mechanistic investigations of a palladium-catalyzed annulation of secondary alkyl iodides

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL BONDS; PALLADIUM; STEREOCHEMISTRY;

EID: 34247860930     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603888     Document Type: Article
Times cited : (96)

References (68)
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    • a) Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), 2nd ed., Wiley-VCH, Weinheim, 2004;
    • (2004) Metal-Catalyzed Cross-Coupling Reactions
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    • Eds, M. Beller, C. Bolm 2nd ed, Wiley-VCH, Weinheim
    • b) Transition Metals for Organic Synthesis (Eds.: M. Beller, C. Bolm) 2nd ed., Wiley-VCH, Weinheim, 2004.
    • (2004) Transition Metals for Organic Synthesis
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    • (2002) Chem. Int. Ed , vol.41 , pp. 4137-4137
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    • The reaction with secondary alkyl bromides led to lower yields of the annulated products
    • The reaction with secondary alkyl bromides led to lower yields of the annulated products.
  • 52
    • 34250759263 scopus 로고    scopus 로고
    • The regiochemistry of the double bond isomers was determined by COSY, HSQC, and 1D ROESY NMR spectroscopy.
    • The regiochemistry of the double bond isomers was determined by COSY, HSQC, and 1D ROESY NMR spectroscopy.
  • 53
    • 34250776473 scopus 로고    scopus 로고
    • The configurations of (S)-7 and (R)-1 are solely based on their preparation. See the Supporting Information for details.
    • The configurations of (S)-7 and (R)-1 are solely based on their preparation. See the Supporting Information for details.
  • 54
    • 34250713314 scopus 로고    scopus 로고
    • The absolute configuration of (S)-11a is based on X-ray analysis of a p-bromobenzoate derivative (S)-16. CCDC-619350 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif. See the Supporting Information for details. The absolute configuration of 4 (Scheme 3 b) was not determined, although we propose the R configuration on the basis of the results of this mechanistic study.
    • The absolute configuration of (S)-11a is based on X-ray analysis of a p-bromobenzoate derivative (S)-16. CCDC-619350 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif. See the Supporting Information for details. The absolute configuration of 4 (Scheme 3 b) was not determined, although we propose the R configuration on the basis of the results of this mechanistic study.
  • 55
    • 34250778278 scopus 로고    scopus 로고
    • CCDC-619351 [(R)-6] and CCDC-627191 [(R)-15] contain 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.
    • CCDC-619351 [(R)-6] and CCDC-627191 [(R)-15] contain 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.
  • 56
    • 34250735525 scopus 로고    scopus 로고
    • On the basis of the synthesis of 7, we believe its absolute configuration to be S. We have determined by X-ray crystallography that the configuration of 11a is S, which indicates that the annulation of oxygen-containing substrates also proceeds with overall inversion
    • On the basis of the synthesis of 7, we believe its absolute configuration to be S. We have determined by X-ray crystallography that the configuration of 11a is S, which indicates that the annulation of oxygen-containing substrates also proceeds with overall inversion.
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    • Angew. Chem. Int. Ed. 2002, 41, 3910-3912.
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    • IV intermediates, see: a J. K. Stille, The Chemistry of the Metal-Carbon Bond, 2 (Eds.: F. R. Hartley, S. Patai), Wiley, New York, 1985, ch. 9;
    • IV intermediates, see: a) J. K. Stille, The Chemistry of the Metal-Carbon Bond, Vol. 2 (Eds.: F. R. Hartley, S. Patai), Wiley, New York, 1985, ch. 9;
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    • see also reference [5].
    • b) see also reference [5].
  • 68
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    • N2 versus direct insertion pathways of oxidative addition, see: J. P. Collman, L. S. L. Hegedus, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, CA, 1980, ch. 4.
    • N2 versus direct insertion pathways of oxidative addition, see: J. P. Collman, L. S. L. Hegedus, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, CA, 1980, ch. 4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.