Asymmetric Synthesis of Dihydronaphthoquinones Containing Adjacent Stereocenters via a Sulfa-Michael Addition Triggered Ring-Expansion Approach

A novel asymmetric synthetic approach for the construction of enantioenriched functionalized dihydroquinones incorporating adjacent quaternary and tertiary stereocenters has been reported, in which enantioenriched 3-allylic phthalides engaged in an unprecedented sulfa-Michael addition-triggered stereoselective ring-expansion reaction, and furnished the desired sulfur-incoporated dihydronaphthoquinones with high stereoselectivity.本研究报道了一种用于构建兼具相邻季碳与叔碳立体中心的对映富集型官能化二氢醌的新型不对称合成方法：该方法以对映富集的3-烯丙基苯酞为反应底物，通过前所未有的硫杂-Michael加成触发的立体选择性扩环反应，最终以高立体选择性得到目标含硫二氢萘醌类化合物。