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Volumn 43, Issue 30, 2004, Pages 3941-3944

Asymmetric catalytic coupling of organoboranes, alkynes, and imines with a removable (trialkylsilyloxy)ethyl group - Direct access to enantiomerically pure primary allylic amines

Author keywords

Alkynes; Allylic amines; Asymmetric catalysis; Imines; Nickel

Indexed keywords

CATALYSTS; CRYSTALLIZATION; DERIVATIVES;

EID: 4544296892     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460044     Document Type: Article
Times cited : (145)

References (41)
  • 4
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    • note
    • N-Diphenylphosphinoylimines and N-tosylimines do not undergo three-component coupling. N-Aryl imines and N-benzylimines afforded low yields and selectivities.
  • 11
  • 16
    • 0000862669 scopus 로고    scopus 로고
    • g) for a review of catalytic, enantioselective additions to imines, see: a) S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069.
    • (1999) Chem. Rev. , vol.99 , pp. 1069
    • Kobayashi, S.1    Ishitani, H.2
  • 19
    • 0000832159 scopus 로고
    • c) for the rearrangement of chiral allylic alcohols to trichloroacetimidates, see: L. E. Overman, J. Am. Chem. Soc. 1974, 96, 597;
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 597
    • Overman, L.E.1
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  • 28
    • 0037471214 scopus 로고    scopus 로고
    • S. J. Patel, T. F. Jamison, Angew. Chem. 2003, 115, 1402; Angew. Chem. Int. Ed. 2003, 42, 1364.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1364
  • 29
    • 4544280998 scopus 로고    scopus 로고
    • note
    • A maximum of 41 % ee and 36 % yield was observed; see reference [9].
  • 30
    • 4544260809 scopus 로고    scopus 로고
    • note
    • P,N ligands, (R)-MOP (2-(diphenylphosphanyl)-2′-methoxy-1,1′- binaphthyl), PPF-OMe ((R)-1-[(S)-2-(diphenylphosphanyl)ferrocenyl]ethyl methyl ether), imidazolium carbenes, and menthol-derived phosphanes are examples of monophosphane ligands tested.
  • 31
    • 4544339825 scopus 로고    scopus 로고
    • note
    • Replacement of the aliphatic group on nitrogen with p-anisyl resulted in lower enantioselectivity (35% ee) with ligand ld under otherwise identical reaction conditions.
  • 33
    • 0037178489 scopus 로고    scopus 로고
    • 2-tert-Butylphenyllithium and 2,6-dimethylphenyllithium did not undergo addition to the oxazaphospholidine-borane complex. Other research groups have reported similar difficulties with mesityllithium, 9-anthryllithium, and 2,4,6-trimethoxyphenyllithium: a) F. Maienza, F. Spindler, M. Thommen, B. Pugin, C. Malan, A. Mezzetti, J. Org. Chem. 2002, 67, 5239.
    • (2002) J. Org. Chem. , vol.67 , pp. 5239
    • Maienza, F.1    Spindler, F.2    Thommen, M.3    Pugin, B.4    Malan, C.5    Mezzetti, A.6
  • 34
    • 0000683974 scopus 로고    scopus 로고
    • In general, additions to imines derived from enolizable aldehydes suffer from deprotonation and decomposition. For recent references, see: a) K. Yamada, S. J. Harwood, H. Groger, M. Shibasaki, Angew. Chem. 1999,111, 3713; Angew. Chem. Int. Ed. 1999, 38, 3504;
    • (1999) Angew. Chem. , vol.111 , pp. 3713
    • Yamada, K.1    Harwood, S.J.2    Groger, H.3    Shibasaki, M.4
  • 35
    • 0033521210 scopus 로고    scopus 로고
    • In general, additions to imines derived from enolizable aldehydes suffer from deprotonation and decomposition. For recent references, see: a) K. Yamada, S. J. Harwood, H. Groger, M. Shibasaki, Angew. Chem. 1999,111, 3713; Angew. Chem. Int. Ed. 1999, 38, 3504;
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 3504
  • 37
    • 4544331705 scopus 로고    scopus 로고
    • ref. [4]
    • c) ref. [4].
  • 40
    • 4544304736 scopus 로고    scopus 로고
    • note
    • a) Reference [4b,c] and references therein;


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.