Formal Asymmetric Catalytic Thiolation with a Bifunctional Catalyst at a Water–Oil Interface: Synthesis of Benzyl Thiols |
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Authors: | Wengang Guo Bo Wu Dr Xin Zhou Ping Chen Xu Wang Prof Yong‐Gui Zhou Prof Yan Liu Prof Can Li |
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Institution: | State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023 (China) |
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Abstract: | The enantioselective conjugated addition of tritylthiol to in situ generated ortho‐quinone methides (o‐QMs) is catalyzed by an acid–base bifunctional squaramide organocatalyst. The transformation proceeds with high yield (up to 99 %) and stereoselectivity (up to 97:3 e.r.) using water as solvent under mild conditions. The catalyst system provides a new strategy for the synthesis of optically active benzyl mercaptans. Control experiments suggested that o‐QMs are generated by the tertiary amine moiety of the squaramide organocatalyst and that the water–oil biphase is crucial for achieving high reactivity and stereoselectivity. |
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Keywords: | asymmetric catalysis organocatalysis ortho‐quinone methides thiol addition |
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