Asymmetric inductive effects have been measured on the Diels-Alder reaction of dimethyl fumarate with o-quinodimethane bearing a chiral u-alkoxy group. The chiral substituents used were f-phenylethoxy, 2-(1-phenyl)propoxy, 1-(2\_phenyl)propoxy, 2-(4-phenyljbutoxy and l-cyclohexylethoxy. The greatest
Asymmetric induction in the diels-alder reactions of α-hydroxyacylnitroso compounds
✍ Scribed by Gordon W. Kirby; Muhammad Nazeer
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- French
- Weight
- 127 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Transient, chiral u-hydroxyacylnitroso compounds (2), able to form intramolecular hydrogen bonds, react stereoselectively with cyclopentadiene and cyclohexa-1,3-diene; the cycloadduct (6) of the latter diene and the nitroso derivative of (S)-mandelic acid has been converted into the known (-)-oxazine derivative .( 9).
📜 SIMILAR VOLUMES
The Diels -Alder reaction of 1,3-cyclohexadiene (9) with the enanticmerically pure cc-chloronitroso compound 8, synthesized from epiandrosterone-(7a), gives the adduct 10a with l-(R),4-(S) configuration-in 69 % chemical yield andz95 % enazicmeric excess.
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