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

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posted on 01.05.2015, 00:00 by Zhi-Peng Hu, Zhe Zhuang, Wei-Wei Liao
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.