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.
Ene reactions with α-chloronitroso compounds: Asymmetric synthesis of N-allylhydroxylamines
✍ Scribed by G. Kreße; H. Felber; A. Ritter; B. Ascherl; A. Vasella
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- English
- Weight
- 364 KB
- Volume
- 105
- Category
- Article
- ISSN
- 0165-0513
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## Abstract The α‐chloronitroso compounds **1a–1f** were made to react with methyl and phenyl Grignard reagents. N‐methyl and N‐phenyl substituted ketonitrones **2** and **3** were obtained in 48‐78% yield. The structure of these labile nitrones is based on their spectroscopic properties and on the
The Diels-Alder reaction of 1,3-cyclohexadiene with the a-chloro-a-nitroso ether 2, prepared from mannose via the lactone oxime 1, gives the adduct 3 with l-(S),4-(R) configuration in 69 % chemical yield and z 95 % enantiome& excess.