Desymmetrizing asymmetric epoxidations of bis(cis-configured) divinylcarbinols: Unusual syn-selectivity combined with ee-enhancement through kinetic resolution

Synlett

Volumn , Issue 1, 2006, Pages 33-38

  Kramer, Rainer ^a   Brückner, Reinhard ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

1,4 Pentadien 3 ols; Diastereoselectivity; Enantioselectivity; Epoxy alcohols; Kinetic resolution

Indexed keywords

1,4 PENTADIEN 3 OL; ALCOHOL DERIVATIVE; DIVINYLCARBINOL DERIVATIVE; EPOXIDE; METHANOL DERIVATIVE; TARTARIC ACID DERIVATIVE; TERT BUTYL ALCOHOL; TITANIUM; UNCLASSIFIED DRUG; VINYL DERIVATIVE; ZIRCONIUM DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SHARPLESS EPOXIDATION; STEREOCHEMISTRY;

EID: 30544446054     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-922778     Document Type: Article

References (47)

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29. 13C NMR spectra and provided correct combustion analyses (C and H ± 0.4%).
30. R = 53.4 min for ent-syn-1a.
31. 1H NMR signal of the minor diastereomer could not be detected.
32. R = 27.8 min for ent-syn-1b.
33. 7 (416.5): C, 66.33; H, 6.78. Found: C, 66.14; H, 6.83.
34. 11
35. 1H NMR spectra allowed determining the yields of the constituents syn-1a, 2a, and 5 of these mixtures.
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41. 4 (266.3): C, 67.64; H, 8.33. Found: C, 67.41; H, 8.52.
42. R = 52.7 min for ent-anti-6.
43. 2,3 = 2.7 Hz, 2-H (anti-6)].
44. R = 26.4 min for ent-syn-6.
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47. 4,6 = 1.0 Hz.