Conformational effects of acetolysis of bicyclo[3.2.0]hept-6-en-2-yl and bicyclo[3.2.0]hept-2-yl derivatives. Homoallylic participation vs. .sigma. participation
β Scribed by Yano, Kazuyuki; Isobe, Masayoshi; Yoshida, Kitaro
- Book ID
- 125966840
- Publisher
- American Chemical Society
- Year
- 1978
- Tongue
- English
- Weight
- 665 KB
- Volume
- 100
- Category
- Article
- ISSN
- 0002-7863
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π SIMILAR VOLUMES
The title compound, C 32 H 31 N 3 O 4 S, is an important intermediate in the synthesis of cephem compounds, which can be converted into broad-spectrum cephalosporin antibiotics. Intermolecular C-HΓ Γ ΓO and C-HΓ Γ ΓS contacts are observed in the crystal structure.
Single crystal X-ray diffraction analysis of compounds A, B and, C helped us to assign the absolute configurations of the enantiomers of the bicyclo[3.2.0]hept-3-en-6-endo-ols 4-6. These bicyclic alcohols were easily obtained by: (i) stereoselective reductions of the bicyclo[3.2.0]hept-3-en-6-ones 1