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Volumn 68, Issue 19, 2003, Pages 7379-7385

Concise synthesis, preparative resolution, absolute configuration determination, and applications of an atropisomeric biaryl catalyst for asymmetric acylation

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ISOMERS; SYNTHESIS (CHEMICAL);

EID: 0141454930     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034603f     Document Type: Article
Times cited : (117)

References (80)
  • 63
    • 0141472599 scopus 로고    scopus 로고
    • note
    • Our inability to form the hindered biaryl axis of biaryl (±)-1 by direct coupling previously led us to develop an indirect synthesis that proceeded via two sequential less hindered coupling reactions. See ref 9e.
  • 64
    • 0034614046 scopus 로고    scopus 로고
    • Buchwald's phenanthryl ligand 4 was the only ligand that allowed coupling between bromopyridine 2 and boronic acid 3. See: (a) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 12051-12052; (b) Yin, J.; Rainka, M. P.; Zhang, X.-X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162-1163.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 12051-12052
    • Yin, J.1    Buchwald, S.L.2
  • 65
    • 0037138687 scopus 로고    scopus 로고
    • Buchwald's phenanthryl ligand 4 was the only ligand that allowed coupling between bromopyridine 2 and boronic acid 3. See: (a) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 12051-12052; (b) Yin, J.; Rainka, M. P.; Zhang, X.-X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162-1163.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 1162-1163
    • Yin, J.1    Rainka, M.P.2    Zhang, X.-X.3    Buchwald, S.L.4
  • 67
    • 0141695866 scopus 로고    scopus 로고
    • note
    • NAr.
  • 71
    • 0141695865 scopus 로고    scopus 로고
    • note
    • The transformation of dihalopyridine 6 into aminopyridines 1 and 7 can be performed as a single step by employing s-BuLi (1.5 equiv) to effect bromine-lithium exchange at -78 °C (30 min), followed by addition of lithium diethylamide (3 equiv), warming to room temperature, and then refluxing for 16 h. However, in our hands this procedure gave a significantly less clean reaction and provided lower yields of the both products following tedious purification.
  • 72
    • 0033411291 scopus 로고    scopus 로고
    • This method of resolving agent selection has been used previously to identify an appropriate chiral amine from a panel of chiral amines for resolution of a racemic carboxylic acid; see: Dyer, U. C.; Henderson, D. A.; Mitchell, M. B. Org. Proc. Res. Devel. 1999, 3, 161-165. This publication also provides a detailed description of the basis of the method and details of the Resolution Companion software package.
    • (1999) Org. Proc. Res. Devel , vol.3 , pp. 161-165
    • Dyer, U.C.1    Henderson, D.A.2    Mitchell, M.B.3
  • 73
    • 0003942864 scopus 로고
    • Wiley: New York
    • The fused benzenoid ring takes priority over the 2-phenyl substituent when assigning the naphthyl end of the biaryl axis by Cahn-Ingold-Prelog (CIP) priority rules; see: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; p 107.
    • (1994) Stereochemistry of Organic Compounds , pp. 107
    • Eliel, E.L.1    Wilen, S.H.2
  • 74
    • 0141695864 scopus 로고    scopus 로고
    • note
    • a)-1 displays a negative Cotton-effect peak in its circular dichroism spectrum at 335 nm. The assignment of the absolute configuration oftopologically related atropisomeric catalyst structures is therefore possible by comparison of their Cotton-effect peaks in this region.
  • 79
    • 0141807258 scopus 로고    scopus 로고
    • note
    • Interestingly, although many of the catalysts studied by Campbell (e.g. structure VI, Figure 1) are topologically closely related to the catalyst of Fuji (structure IV, Figure 1), H-bonding was postulated to be the dominant mediator of chirality transfer for this series of catalysts and no evidence for π-π stacking was found. See ref 7a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.