Anion effect on enantioselective oxidative NHC catalysis: highly efficient kinetic resolution of tertiary alcohols and beyond†

Dan Hu , Si Bei Poh , Feipeng Liu , Zhifeng Tu , Xia Wang , Shenci Lu , Yu Zhao
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Abstract

The effect of the counter-anion in the azolium pre-catalyst on enantio-control in oxidative NHC catalysis is demonstrated systematically for the first time in acylative kinetic resolution of oxindole-derived tertiary alcohols.

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阴离子对对映选择性氧化NHC催化的影响:叔醇及以上的高效动力学拆分†
首次系统地论证了反阴离子在氧化NHC催化中对映体控制的作用。对于通过NHC催化的酯化反应动力学拆分羟吲哚衍生的叔醇,阴离子的身份,无论是以添加剂的形式还是作为唑鎓预催化剂中的反阴离子,都对催化体系的对映选择性有显著影响。通过适当选择阴离子,对于具有烷基、芳基和官能化取代基的广泛的环氧吲哚衍生的叔醇实现了高效的动力学拆分(krel在30和>;200之间)。阴离子对其他氧化NHC催化过程如形式环加成的影响也得到了证明。
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Synthesis of biologically active [1,5]diazocino[2,1-b]quinazolinones through [4 + 4] cycloaddition of 2-alkynyl quinazolinones with aza-ortho-quinone methides† Synthesis of fluorinated allylic alcohols via photoinduced decarboxylative cross-coupling of α-fluoroacrylic acids and alcohols† Aromatization-driven cascade [1,5]-hydride transfer/cyclization for synthesis of spirochromanes† Playing with the cavity size of exTTF-based self-assembled cages† An alternative approach to triazatruxene synthesis and derivatization to a boron difluoride complex†
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