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Electroreductive Coupling of Optically Active α,β-Unsaturated Carbonyl Compounds with Diaryl Ketones: Asymmetric Synthesis of 4,5,5-Trisubstituted γ-Butyrolactones

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posted on 20.06.2014, 00:00 by Naoki Kise, Yusuke Hamada, Toshihiko Sakurai
The electroreductive coupling of optically active N-E-crotonoyl- and N-cinnamoylimidazolidin-2-ones and oxazolidin-2-ones with diaryl ketones in the presence of chlorotrimethylsilane gave adducts with high diastereoselectivity. The adducts were readily transformed to optically active 4,5,5-trisubstituted γ-butyrolactones by treatment with TBAF.

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