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Volumn 134, Issue 41, 2012, Pages 17003-17006

Catalytic enantioselective cross-couplings of secondary alkyl electrophiles with secondary alkylmetal nucleophiles: Negishi reactions of racemic benzylic bromides with achiral alkylzinc reagents

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIC; CROSS-COUPLING PRODUCTS; CROSS-COUPLINGS; ELECTROPHILES; ENANTIOSELECTIVE; NEGISHI REACTIONS;

EID: 84867556242     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja308460z     Document Type: Article
Times cited : (158)

References (37)
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    • Nickel-catalyzed (activated electrophile)
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    • For a recent application in the total synthesis of carolacton (enantioselective Negishi cross-coupling of a racemic allylic chloride), see: Schmidt, T.; Kirschning, A. Angew. Chem., Int. Ed. 2012, 51, 1063-1066
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    • Schmidt, T.1    Kirschning, A.2
  • 15
    • 0037021014 scopus 로고    scopus 로고
    • For an example of a cobalt-catalyzed asymmetric coupling of a tertiary alkyl bromide with an allylmagnesium reagent that proceeds in 22% ee and 49% yield, see: Tsuji, T.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2002, 41, 4137-4139
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 4137-4139
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  • 24
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    • Brunner, H.1    Obermann, U.2
  • 26
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    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 6902-6905
    • Kikushima, K.1    Holder, J.C.2    Gatti, M.3    Stoltz, B.M.4
  • 27
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    • (2009) Chem. Rev. , vol.109 , pp. 2505-2550
    • Hargaden, G.C.1    Guiry, P.J.2
  • 29
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    • Possible explanations for the beneficial effect of the halide salt include in situ formation of a benzylic iodide and the generation of more reactive zincate complexes. For a recent discussion and leading references regarding zincate adducts, see: McCann, L. C.; Hunter, H. N.; Clyburne, J. A. C.; Organ, M. G. Angew. Chem., Int. Ed. 2012, 51, 7024-7027
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  • 34
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    • For a report of primary-to-secondary isomerization (2%) in a palladium -catalyzed Negishi reaction, see: Han, C.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 7532-7533
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 7532-7533
    • Han, C.1    Buchwald, S.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.