Chiral Tertiary Sulfonium Salts as Effective Catalysts for Asymmetric Base-Free Neutral Phase-Transfer Reactions

Chiral Tertiary Sulfonium Salts as Effective Catalysts for Asymmetric Base-Free Neutral Phase-Transfer Reactions
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DOI:
10.1002/anie.201612328
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发表时间:
2017-04-18
影响因子:
16.6
通讯作者:
Shirakawa, Seiji
Shirakawa, Seiji
中科院分区:
化学1区
文献类型:
--
作者:
Liu, Shiyao;Maruoka, Keiji;Shirakawa, Seiji

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虽然手性季铵盐和鏻盐通常用于不对称有机催化,但手性叔锍盐的催化能力在不对称合成中尚未得到证实。在此,我们表明,手性双官能三烷基锍盐催化3-取代羟吲哚马来酰亚胺在无碱中性相转移条件下的高度对映选择性共轭加成。
Although chiral quaternary ammonium and phosphonium salts are commonly used for asymmetric organocatalysis, the catalytic ability of chiral tertiary sulfonium salts has yet to be demonstrated in asymmetric synthesis. Herein, we show that chiral bifunctional trialkylsulfonium salts catalyze highly enantioselective conjugate additions of 3-substituted oxindoles to maleimides under base-free neutral phase-transfer conditions.