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Catalytic Asymmetric Sulfenylation to Structurally Diverse Dithioketals

Liao  Kui  Zhou  Feng  Zhou  Jian  
【摘要】:Over the past few years,despite ongoing processes in the synthesis of chiral secondary and tertiary thiol derivatives,very limited attention is paid to the enantioselective synthesis of optically active dithioketals,However,besides their synthetic applications,an increasing number of researches reveal that the dithioketal motifs have promising potential for the research and development of new biopharmaceutics.In this context,as well as the importance of chirality in medicinal research,it is highly desirable to develop efficient methods to chiral dithioketals.Inspired by the pioneering work of Gulea1 a and J?rgensen~(1b) in the catalytic asymmetric synthesis of chiral dithioketals via the thio-Diels-Alder reaction,together with our efforts in enantioselective construction of S-containing tetrasubstituted carbon stereocenters,2 we developed the first highly enantioselective synthesis of dithioketals via catalytic asymmetric sulfenylation of S-based active methine compounds,which provides a facile method for the synthesis of a variety of structurally diverse chiral dithioketals,including those bearing a SCF_3 group.Importantly,this work brings into attention that the ambident nucleophility of S-based nucleophiles may lead to severe side reactions,an untrodden issue as for the use of S-based nucleophiles to develop asymmetric reactions.

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