ChemInform Abstract: Asymmetric Induction via an Intramolecular Haloetherification Reaction of Chiral Ene Acetals: A Novel Approach to Optically Active 1,4- and 1, 5-Diols.
✍ Scribed by H. FUJIOKA; H. KITAGAWA; Y. NAGATOMI; Y. KITA
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 35 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Asymmetric Induction via an Intramolecular Haloetherification Reaction of Chiral Ene Acetals: A Novel Approach to Optically Active 1,4-and 1, 5-Diols.
-A new asymmetric synthesis of chiral 1,4-(XVI) and 1,5-diols (XVIII) is developed based on remote asymmetric induction of 2 stereogenic centers into the ene acetals (I) and (VII) as key steps. The formation of a bicyclic cationic intermediate is responsible for the high stereoselectivity of the reaction. In the subsequent nucleophilic replacement of the alkoxy group of (IX) and (XII), the methoxyethoxy group is essential. Diol (XVIII) is the starting compound for an already described synthesis of Solenopsin A, a constituent of the venom of a fire ant. -(FUJIOKA, H.;