Although frustrated Lewis pair (FLP) chemistry has found numerous applications, FLPs are best known for their utility in catalytic, metal-free reductions. In the last decade, FLP catalysts have been applied to a wide range of substrates, and a few efficient chiral FLP catalysts achieving highly stereoselective reductions have emerged. Nonetheless, access to such metal-free catalysts typically involves multi-step and synthetically challenging processes, thus precluding wider use. In this work, we report facile access to a family of chiral FLP catalysts via the hydroboration of derivatives of a commercially available steroid precursor. These catalysts are shown to be highly selective catalysts for the enantioselective hydrosilylation of imines and quinolines, producing chiral amines and tetrahydroquinolines.

尽管受阻路易斯对 (FLP) 化学已找到许多应用，但 FLP 最出名的是其在催化、无金属还原方面的用途。在过去的十年中，FLP催化剂已应用于广泛的底物，并且出现了一些实现高度立体选择性还原的高效手性FLP催化剂。尽管如此，获得这种无金属催化剂通常涉及多步骤且具有合成挑战性的过程，因此阻碍了更广泛的使用。在这项工作中，我们报告了通过市售类固醇前体衍生物的硼氢化反应，可以轻松获得一系列手性 FLP 催化剂。这些催化剂被证明是用于亚胺和喹啉的对映选择性氢化硅烷化的高选择性催化剂，产生手性胺和四氢喹啉。