Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, ON, Canada M5S 3H6.
J Org Chem. 2016 Aug 5;81(15):6774-8. doi: 10.1021/acs.joc.6b00782. Epub 2016 Jul 14.
The first catalytic method for the selective 1,4-conjugate allylation of α,β-unsaturated aldehydes is reported. The method employs an air-stable diethanolamine-complexed boronic acid (DABO boronate) as the allyl transfer reagent and promotes conjugate addition over 1,2-addition. A variety of aryl- and alkyl-substituted enals are tolerated, providing δ,ε-unsaturated aldehyde products in good yields and selectivities under mild conditions.
首次报道了一种对α,β-不饱和醛进行选择性 1,4-共轭烯丙基化的催化方法。该方法采用空气稳定的二乙醇胺配合硼酸（DABO 硼酸酯）作为烯丙基转移试剂，促进共轭加成而不是 1,2-加成。该方法能够容忍各种芳基和烷基取代的烯醛，在温和条件下以良好的收率和选择性得到 δ,ε-不饱和醛产物。
