Tetrahedron: Asymmetry

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 …

M Murakami, H Kamaya, C Kaneko, M Sato

Index: Murakami, Masayuki; Kamaya, Hiroshi; Kaneko, Chikara; Sato, Masayuki Tetrahedron Asymmetry, 2003 , vol. 14, # 2 p. 201 - 215

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Citation Number: 14

Abstract

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. ...