Solvent-dependent stereochemical anomaly in the nucleophilic addition of ester-derived enolate to bicyclo[3,3,0]octan-2-one system of diacetone glucos-3-ulose

Chemistry Letters

Volumn , Issue 6, 1998, Pages 475-476

  Yamauchi, Noriaki ^a   Kishida, Masashi ^b   Sawada, Keiju ^b   Ohashi, Yuji ^b   Eguchi, Tadashi ^b   Kakinuma, Katsumi ^b  

^a YAMAGATA UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032364306     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.475     Document Type: Article

References (17)

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14. 3), 3.71 (1H, d, J = 8.8 Hz, 4-H), 3.86 (1H, dd, J = 5.7 , 8.4 Hz, 6-H), 4.10 (1H, dd, J = 5.7, 8.4 Hz, 6-H), 4.44 (1H, dt, J = 8.8, 5.7 Hz, 5-H), 4.80 (1H, d, J = 3.9 Hz, 2-H) 5.58 (1H, d, J = 3.9 Hz, 1-H). NOEs were observed at 1-H and 2-H proton signals by irradiation of 1′-H resonance.
15. M. Kishida, N. Yamauchi, K. Sawada, Y.Ohashi, T. Eguchi, and K. Kakinuma, Perkin 1, 891 (1997).
16. 3): δ 1.29 (3H, s), 1.34 (3H, s), 1.43 (3H, s), 1.52 (3H, s), 1.83 (3H, s), 3.62 (1H, s, -OH), 3.76 (1H, s), 3.96 (1H, dd, J = 7.0, 8.9 Hz, 6-H), 4.07 (1H, dd, J = 7.2, 8.9 Hz, 6-H), 4.31-4.25 (2H, m, 4-H and 5-H), 4.32 (1H, d, J = 3.9 Hz, H-2), 5.07 (1H, s, vinyl H), 5.11 (1H, s, vinyl H), 5.94 (1H, d, J = 3.9 Hz, 1-H).
17. 3, The measurement was made by Rigaku AFC5R diffractometer with graphite monochromated Cu-Kα radiation (λ=1.54184 Å). The structure was solved by direct method (Shelxs86). Refinement by full-matrix least-squares calculations (Shelx197) converged at R=0.044 for 1477 observed reflections with I>2sigma(I).