Computational studies with density functional theory (DFT) indicate that the supposedly “weak” C−H⋅⋅⋅S noncovalent interaction is the primary reason why enantioselectivity is reversed form R to S in the thiocyanation reaction with the asymmetric cinchona alkaloid complex (BzCPD) catalyst, when the nucleophile is changed from β-keto ester to oxindole. Since there are many asymmetric transformations that involve the sulphur heteroatom, the current findings have considerable relevance.

中文翻译：

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“弱”C−H⋅⋅⋅S 相互作用驱动金鸡纳生物碱复合物催化硫氰化反应的对映选择性

密度泛函理论 (DFT) 的计算研究表明，所谓的“弱”C−H⋅⋅⋅S 非共价相互作用是在与不对称金鸡纳生物碱复合物 (BzCPD) 的硫氰化反应中对映选择性从 R 反转为 S 的主要原因当亲核试剂从β-酮酯转变为羟吲哚时，催化剂。由于存在许多涉及硫杂原子的不对称转变，因此当前的发现具有相当大的相关性。