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Volumn 70, Issue 16, 2005, Pages 6137-6151

Chiral oxazolines and their legacy in asymmetric carbon-carbon bond-forming reactions

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; ALKYLATION; AMINO ACIDS; CARBON; CHEMICAL BONDS; COMPLEXATION; ORGANOMETALLICS;

EID: 23044473699     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050470h     Document Type: Review
Times cited : (126)

References (121)
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    • 2-Oxazolines
    • Palmer, D., Ed.; J. Wiley and Sons: Hoboken, NJ, Oxazoles
    • (g) Wong, G. S. K.; Wu, W. 2-Oxazolines. In Chemistry of Heterocyclic Compounds; Palmer, D., Ed.; J. Wiley and Sons: Hoboken, NJ, 2004; Vol. 60, Oxazoles, Part B.
    • (2004) Chemistry of Heterocyclic Compounds , vol.60 , Issue.PART B
    • Wong, G.S.K.1    Wu, W.2
  • 20
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    • An article describing early work on this subject has been published: Meyers, A. I. Acc. Chem. Res. 1979, 11 375.
    • (1979) Acc. Chem. Res. , vol.11 , pp. 375
    • Meyers, A.I.1
  • 31
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    • Cram, D. J.; Wilson, D. R. J. Am. Chem. Soc. 1963, 85, 1245. For a further discussion of the cyclic model see ref 1 above, pp 94-112.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 1245
    • Cram, D.J.1    Wilson, D.R.2
  • 35
    • 33544461247 scopus 로고
    • US Patent 3,935,280
    • There were a number of claims that metal hydrides reduce amino acids with varying degrees of racemization and that boranes were superior reducing agents in this regard. Lane, C. F. US Patent 3,935,280; Chem. Abstr. 1976, 84, 135101p.
    • (1976) Chem. Abstr. , vol.84 , pp. 135101
    • Lane, C.F.1
  • 48
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    • Non catalytic additions to unsaturated carbonyl compounds
    • Morrison, J. D., Ed.; Academic Press: New York
    • For a discussion on a number of early chelate-assisted asymmetric additions to conjugated unsaturated carbonyl in the late 1970s and early 1980s, see: Tomioka, K.; Koga, K. Non Catalytic Additions to Unsaturated Carbonyl Compounds. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol 2, Part.
    • Asymmetric Synthesis , vol.2 , Issue.PART , pp. 1983
    • Tomioka, K.1    Koga, K.2
  • 61
    • 18844402515 scopus 로고    scopus 로고
    • Chiral bis(oxazolines)
    • Palmer, D. C., Ed.; J. Wiley and Sons: Hoboken, NJ, "Oxazoles"
    • Ghosh, A. K.; Bilcer, G.; Fidanze, S. Chiral Bis(Oxazolines). In The Chemistry of Heterocyclic Compounds; Palmer, D. C., Ed.; J. Wiley and Sons: Hoboken, NJ, 2004; Vol. 60, "Oxazoles", Part B.
    • (2004) The Chemistry of Heterocyclic Compounds , vol.60 , Issue.PART B
    • Ghosh, A.K.1    Bilcer, G.2    Fidanze, S.3
  • 63
    • 2142854868 scopus 로고    scopus 로고
    • Academic Press: New York
    • Compendium of Chiral Auxiliary Applications; Roos, G., Ed.; Academic Press: New York, 2002. This is a three-volume extensive tabular treatment on chiral auxiliaries and their application to organic reactions.
    • (2002) Compendium of Chiral Auxiliary Applications
    • Roos, G.1
  • 64
    • 0001161530 scopus 로고
    • Ortho-metalation of aryloxazolines have been described previously: Meyers, A. I.; Mihelich, E. D. J. Org. Chem. 1975, 40, 3158.
    • (1975) J. Org. Chem. , vol.40 , pp. 3158
    • Meyers, A.I.1    Mihelich, E.D.2
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    • Organolithiums: Selectivity for synthesis
    • Pergamon Press: New York
    • Claydon, J. Organolithiums: Selectivity for Synthesis. Tetrahedron Organic Chemistry Series; Pergamon Press: New York, 2002; Vol. 23.
    • (2002) Tetrahedron Organic Chemistry Series , vol.23
    • Claydon, J.1
  • 76
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    • and earlier references cited by these authors
    • (a) Richtzenhain, H.; Nippus, P. Chem. Ber. 1949, 82, 408 and earlier references cited by these authors.
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  • 90
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    • For additional reports on the total synthesis of natural biaryls via this route, see: Degnan, A. P.; Meyers, A. I. J. Am. Chem. Soc. 1999, 121, 2762.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 2762
    • Degnan, A.P.1    Meyers, A.I.2
  • 98
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    • Ph.D. Thesis, Colorado State University, 1982
    • Further details are given in Lutomski, K. A. Ph.D. Thesis, Colorado State University, 1982.
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    • Ph.D. Dissertation, Colorado State University, 1984, pp 82-100
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    • Wettlaufer, D.G.1
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    • note
    • References to many studies are mentioned in ref 89 above.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.