Facile Synthesis of Selenium/Sulfur-Substituted 3-Oxa-bicyclo[4.2.0]octa-1(8),5-diene and Tetrahydro-1<i>H</i>-isochromene via Sequential Three-Component Conjugate Addition/Condensation/Elimination/[2 + 2] or [4 + 2] Cyclization Reactions
作者:Jian Cao、Xian Huang、Luling Wu
DOI:10.1021/jo101905r
日期:2011.3.4
selenium/sulfur-substituted 3-oxabicyclo[4.2.0]octa-1(8),5-diene and tetrahydro-1H-isochromene from lithium alkylselenolates or alkylthiolates, 1-alkynylphosphine oxides, and aldehydes. The sequential reaction proceeds via a conjugate addition/condensation/elimination process to form the allene intermediate, which subsequently underwent [2 + 2] or [4 + 2] cyclization reaction to afford bicyclic frameworks
有趣的顺序三组分反应提供了一种从烷基硒酸锂或烷基硫醇盐中轻松合成硒/硫取代的3-氧杂双环[4.2.0] octa-1(8),5-二烯和四氢-1 H-异亚戊二烯的方法,1-炔基膦氧化物和醛。顺序反应通过共轭加成/缩合/消除过程进行,以形成丙二烯中间体,随后对其进行[2 + 2]或[4 + 2]环化反应以提供双环骨架。