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Volumn 60, Issue 20, 2004, Pages 4459-4473

Chiral oxazoline route to enantiomerically pure biphenyls: Magnesio and copper mediated asymmetric hetero- and homo-coupling reactions

Author keywords

Atropisomerism; Chiral biphenyls; Chiral oxazolines; Grignard reagents; Ullmann coupling

Indexed keywords

2,2 (DIFORMYL) 6,6 DIMETHOXY 1,1 BIPHENYL; 2,2 (DIHYDROXYMETHYL) 6,6 DIMETHOXY 1,1 BIPHENYL; 2,2 (DIMETHYL) 6,6 DIMETHOXY 1,1 BIPHENYL; 2,2' (DIHYDROXY) 6,6 DIMETHOXY 1,1' BIPHENYL; 2,2' (DIHYDROXYL) 6,6 DIMETHYL 1,1 BIPHENYL; 2,2' DIHYDROXY 4,5,6,4',5',6' HEXAMETHOXYBIPHENYL; ARGON; BIPHENYL DERIVATIVE; BROMINE; BROMINE DERIVATIVE; COPPER; MAGNESIUM; OXAZOLINE DERIVATIVE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

EID: 1942436903     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.01.095     Document Type: Article
Times cited : (73)

References (60)
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    • Asymmetric synthesis via chiral oxazolines
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    • Meyers A.I., Lutomski K.A. Asymmetric synthesis via chiral oxazolines. Morrison J.D. Asymmetric synthesis III. 1984;Academic, London.
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    • note
    • 8 for making acetals, alcohols, TBDMS, and TIPS derivatives.
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    • For a preliminary report on this study, see:
    • For a preliminary report on this study, see: Moorlag H., Meyers A.I. Tetrahedron Lett. 1993;6989-6993.
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    • Moorlag, H.1    Meyers, A.I.2
  • 24
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    • note
    • Desilylation of the 93:7 mixture of diastereomers in 12h was effected by 2% HF in 10% acetonitrile-water for 1 h at room temperature. The corresponding hydroxy product was completely separated from its diastereomer by radial chromatography on silica (hexane-ethyl acetate). However, it was subsequently found that the silylated derivative 12h could also be separated, and this was, therefore, carried forward to (S)-15.
  • 25
    • 1942445161 scopus 로고    scopus 로고
    • The diastereotopic benzylic protons in the Mosher esters of 16 provided an excellent probe for determining the enantiomeric purity when examined at 300 MHz.
  • 29
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    • Reported in preliminary form, see Ref. 13 above
    • Reported in preliminary form, see Ref. 13 above.
  • 34
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    • See Ref. 36 below.
    • (b) A recent report describes stereochemical stability in biphenyls containing only two ortho substituents, but both capable of metal coordination by chiral oxazolines to Cu(I). See Ref. 36 below.
  • 37
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    • Migration of aryl groups in aldehydes is only seldom seen. In some rare cases, aromatic aldehydes will rearrange to phenyl formates. (a)
    • Migration of aryl groups in aldehydes is only seldom seen. In some rare cases, aromatic aldehydes will rearrange to phenyl formates. (a) Godfrey I.M., Sargent M.V., Elix J.A. J. Chem. Soc., Perkin Trans. 1. 1974;1353.
    • (1974) J. Chem. Soc., Perkin Trans. 1 , pp. 1353
    • Godfrey, I.M.1    Sargent, M.V.2    Elix, J.A.3
  • 39
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    • For some representative examples, see; (a)
    • For some representative examples, see; (a) Lin G.Q., Zhong M. Tetrahedron Lett. 37:1996;3015.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 3015
    • Lin, G.Q.1    Zhong, M.2
  • 44
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    • note
    • t, R-29 =13 min; S-29 =18 min.
  • 51
    • 1942509484 scopus 로고    scopus 로고
    • note
    • RS-33 was obtained by the usual copper mediated Ullmann coupling of 2-bromo-3,5-dimethyl oxazoline and, in this case, gave only a 3:1 mixture of (SSS)-33 and (SSR)-33. It is noteworthy that the R (axial configuration only) diastereomer prevailed slightly under these conditions. This is another example where the nature of the aromatic substituents affected coupling stereochemistry. It also may be that Cu-π interaction is somehow involved in determining stereochemistry.
  • 52
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    • This result was initially reported in 1994:
    • This result was initially reported in 1994: Nelson T.D., Meyers A.I. Tetrahedron Lett. 35:1994;3259.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 3259
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  • 58
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    • A recent report by Chan has also demonstrated that other chiral substrates (chiral 1,3-dioxanes) on the aryl halide can be utilized to form moderately diastereo-enriched biphenyls (7:2) in the Ullmann coupling:
    • A recent report by Chan has also demonstrated that other chiral substrates (chiral 1,3-dioxanes) on the aryl halide can be utilized to form moderately diastereo-enriched biphenyls (7:2) in the Ullmann coupling: Qiu L., Qi J., Pai G., Chan S., Zhou Z., Choi M., Chan A.S.C. Org. Lett. 4:2002;4599.
    • (2002) Org. Lett. , vol.4 , pp. 4599
    • Qiu, L.1    Qi, J.2    Pai, G.3    Chan, S.4    Zhou, Z.5    Choi, M.6    Chan, A.S.C.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.