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Asymmetric induction in the [2+2] cycloaddition of a keteniminium salt: an approach to chiral 13-oxa prostanoids

✍ 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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πŸ“œ SIMILAR VOLUMES


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✍ Pil-Jong Shim; Hee-Doo Kim πŸ“‚ Article πŸ“… 1998 πŸ› Elsevier Science 🌐 French βš– 244 KB

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.

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## Abstract [4+2]Cycloaddition reactions of cyclopentadiene (**1a**) and furan (**1b**) to __N,Nβ€²__‐fumaroyldi[(2__R__)‐bornane‐10,2‐sultam] (**2**) and to __N,Nβ€²__‐fumaroyldi[(2__R__)‐bornane‐10,2‐(2′‐phenyl‐pyrazol‐3′‐one)] (**3**) are presented. A correlation between the solvent polarity and the