Synthesis of optically active 1,3-dioxin-4-one derivatives having a hydroxymethyl group at the 2-position and their use for regio-, diastereo-, and enantioselective synthesis of substituted cyclobutanols
✍ Scribed by Masayuki Murakami; Hiroshi Kamaya; Chikara Kaneko; Masayuki Sato
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- English
- Weight
- 677 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0957-4166
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✦ Synopsis
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. Desymmetrization of the prochiral dioxinones by lipase-catalyzed monoacetylation afforded optically active 2-(hydroxymethyl)dioxinones. Intramolecular photo[2+2]cycloaddition of v-alkenyl esters of these alcohols provided an efficient method for regio-, diastereo-, and enantioselective synthesis of cyclobutanols.