Asymmetric induction in the [2+2] cycloaddition of a keteniminium salt: an approach to chiral 13-oxa prostanoids
β Scribed by Trevor J. Cholerton; Eric W. Collington; Harry Finch; David Williams
- Book ID
- 103401069
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- French
- Weight
- 247 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
Optically active bicyclo[4.2.0]octan-7-ones were synthesized by stereoselective intramolecular [2+2] cycloaddition of alkene-keteniminium salt derived from L-glutamic acid, based on 1,3-asymmelric induction. Synthetic application toward (+)-gibberellic acid key intermediate was also described.
## Abstract [4+2]Cycloaddition reactions of cyclopentadiene (**1a**) and furan (**1b**) to __N,Nβ²__βfumaroyldi[(2__R__)βbornaneβ10,2βsultam] (**2**) and to __N,Nβ²__βfumaroyldi[(2__R__)βbornaneβ10,2β(2β²βphenylβpyrazolβ3β²βone)] (**3**) are presented. A correlation between the solvent polarity and the