Synthesis of 1,3-dioxin-4-ones having a trifluoromethyl group at the 5-position: versatile building blocks for trifluoromethylated compounds
β Scribed by Iwaoka, Tomoyasu; Sato, Masayuki; Kaneko, Chikara
- Book ID
- 121380738
- Publisher
- The Royal Society of Chemistry
- Year
- 1991
- Tongue
- English
- Weight
- 204 KB
- Volume
- 18
- Category
- Article
- ISSN
- 0022-4936
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A new method for preparing optically active 1,3-dioxin-4-one derivatives is presented. A series of prochiral 2,2-bis(hydroxymethyl)-1,3-dioxin-4-ones was synthesized by [4+2]cycloaddition of acylketene to protected 1,3-dihydroxy-2-propanone derivatives followed by deprotection of the hydroxyl groups
An efficient synthesis of diastereomerically pure 5-amino-1,2,3,4-cyclohexanetetrols (6 and 11) and quercitol derivatives from naturally available (+)-proto-quercitol (1) is described. The stereochemistry of 1 is perfectly set up for regioselective protection of the hydroxy group which was further f