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Volumn 64, Issue 24, 2008, Pages 5637-5644

On the influence of chiral auxiliaries in the stereoselective cross-coupling reactions of titanium enolates and acetals

Author keywords

Acetals; Asymmetric synthesis; Chiral auxiliaries; Titanium enolates

Indexed keywords

1,3 OXAZOLIDIN 2 ONE; 1,3 OXAZOLIDINE 2 THIONE; ACETAL DERIVATIVE; BENZALDEHYDE; CARBON SULFUR MONOCYCLE; FUNCTIONAL GROUP; ISOMERASE; N PROPANOYL 1,3 THIAZOLIDINE 2 THIONE; OXAZOLE DERIVATIVE; OXAZOLIDINE DERIVATIVE; OXAZOLIDINETHIONE; OXAZOLIDINONE DERIVATIVE; THIAZOLIDINE DERIVATIVE; TITANIUM DERIVATIVE; TITANIUM ENOLATE;

EID: 43149102475     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.04.044     Document Type: Article
Times cited : (42)

References (47)
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    • For recent contributions, see:
    • For recent contributions, see:
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    • For similar processes based on N-acetyl-1,3-oxazolidine-2-thiones, see:
    • For similar processes based on N-acetyl-1,3-oxazolidine-2-thiones, see:
  • 19
    • 43149104422 scopus 로고    scopus 로고
    • For recent reviews on the synthesis and reactivity of chiral oxazolidinethiones and thiazolidinethiones, see:
    • For recent reviews on the synthesis and reactivity of chiral oxazolidinethiones and thiazolidinethiones, see:
  • 24
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    • For the preparation of thiazolidinethione-like chiral auxiliaries, see:
    • For the preparation of thiazolidinethione-like chiral auxiliaries, see:
  • 26
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    • See Ref. 10.
    • See Ref. 10.
  • 27
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    • note
    • 2 was chosen because its milder character as Lewis acid.
  • 28
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    • note
    • Crystallographic data (excluding structure factors) for this structure has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC-150269. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 (0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
  • 30
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    • -1) on the basis of the different conformational arrangements available for the alternative transition states (for a nice discussion, see:
    • -1) on the basis of the different conformational arrangements available for the alternative transition states (for a nice discussion, see:
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  • 31
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    • 2 relies on kinetic grounds, it may be helpful to consider the phenyl group as the smallest substituent positioned at C4 in the N-propanoyl thiazolidinethiones 3
    • 2 relies on kinetic grounds, it may be helpful to consider the phenyl group as the smallest substituent positioned at C4 in the N-propanoyl thiazolidinethiones 3
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    • note
    • For the effect of the C4 substituent of such chiral auxiliaries in the context of the acetate aldol reaction, see Ref. 8b.
  • 33
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    • An excellent analysis on the steric bulk of the C4 substituent in the addition of the titanium enolates from N-acetyl-1,3-thiazolidine-2-thiones to dimethyl acetals in the course of the total synthesis of (-)-hennoxazole has been recently reported, see:
    • An excellent analysis on the steric bulk of the C4 substituent in the addition of the titanium enolates from N-acetyl-1,3-thiazolidine-2-thiones to dimethyl acetals in the course of the total synthesis of (-)-hennoxazole has been recently reported, see:. Smith T.E., Kuo W.-H., Balskus E.P., Bock V.D., Roizen J.L., Theberge A.B., Carroll K.A., Kurihara T., and Wessler J.D. J. Org. Chem. 73 (2008) 142
    • (2008) J. Org. Chem. , vol.73 , pp. 142
    • Smith, T.E.1    Kuo, W.-H.2    Balskus, E.P.3    Bock, V.D.4    Roizen, J.L.5    Theberge, A.B.6    Carroll, K.A.7    Kurihara, T.8    Wessler, J.D.9
  • 34
    • 43149087566 scopus 로고    scopus 로고
    • Lewis acid-mediated additions of carbon nucleophiles to acetals usually proceed through carbocation intermediates. For example, see:
    • Lewis acid-mediated additions of carbon nucleophiles to acetals usually proceed through carbocation intermediates. For example, see:
  • 40
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    • Unpublished results from Erik Galvez, Ph.D. Thesis in course.
    • Unpublished results from Erik Galvez, Ph.D. Thesis in course.
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    • N2 mechanism. For a nice account on this issue, see:
    • N2 mechanism. For a nice account on this issue, see:. Denmark S.E., and Almstead N.G. J. Am. Chem. Soc. 113 (1991) 8089
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  • 42
    • 43149084624 scopus 로고    scopus 로고
    • For related examples on the influence of C4 substituents on the structure of several enolates, see:
    • For related examples on the influence of C4 substituents on the structure of several enolates, see:
  • 45
    • 2142757265 scopus 로고    scopus 로고
    • For the crucial role played by the exocyclic sulfur atom in the addition of titanium enolates from N-acetyl-1,3-oxazolidine-2-thiones to 2,5-disubstituted tetrahydrofurans, see:
    • For the crucial role played by the exocyclic sulfur atom in the addition of titanium enolates from N-acetyl-1,3-oxazolidine-2-thiones to 2,5-disubstituted tetrahydrofurans, see:. Jalce G., Seck M., Franck X., Hocquemiller R., and Figadère B. J. Org. Chem. 69 (2004) 3240
    • (2004) J. Org. Chem. , vol.69 , pp. 3240
    • Jalce, G.1    Seck, M.2    Franck, X.3    Hocquemiller, R.4    Figadère, B.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.