Use of 1,3-dioxin-4-ones and related compounds in synthesis, Part 50. 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

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)dioxin ones. Intramolecular photo[2+2]cycloaddition of W-alkenyl esters of these alcohols provided an efficient method for regio-, diastereo-, and enantio selective synthesis of cyclobutanols. (C) 2003 Elsevier Science Ltd. All rights reserved.