Regulation of diastereoselectivity through the epimerisation of a cyclic intermediate in the reaction of cyclic ketene ortho ester with aldehydes

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 21, 2000, Pages 3622-3626

  Yu, Chan Mo ^a   Lee, Jac Young ^a   Chun, Kwangwoo ^a   Lee, Junhee ^a   Lee, Yong Am ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYSIS; HYDROLYSIS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CHEMICAL TRANSFORMATIONS;

ESTERS;

EID: 0034619658     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b005086p     Document Type: Article

References (17)

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4. M. T. Reetz, Chem. Rev., 1999, 99, 1121.
5. For general discussions, see: M. Nogradi, Stereoselective Synthesis, 2nd edn., VCH, Weinheim, 1995;
6. R. S. Atkinson, Stereoselective Synthesis, Wiley, New York, 1995.
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13. (b) C.-M. Yu, W.-H. Jung, H.-S. Choi, J. Lee and J.-K. Lee, Tetrahedron Lett., 1995, 36, 8255.
14. During the investigation, we tried to isolate intermediates 5 and 6 under various neutral or basic conditions, but were unsuccessful. The major component was always 2 or 3 along with several minor components. However, after mild acidic work up, 2 and 3 could be obtained cleanly.
15. Compound 1 was prepared according to the established procedure in ref. 5(a), and also see: M. Schlosser, in Organometallics in Synthesis, ed. M. Schlosser, John Wiley & Son, New York, 1994, pp. 1-166;
16. L. Brandsma and H. Verkruijsse, Preparative Polar Organometallic Chemistry, vol. 1, Springer-Verlag, Berlin, 1987, p. 86.
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