Dipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, I-20133 Milano, Italy.
Beilstein J Org Chem. 2013 Apr 2;9:633-40. doi: 10.3762/bjoc.9.71. Print 2013.
The behavior of readily synthesized and even commercially available (S)-proline derivatives, was studied in the trichlorosilane-mediated reduction of ketoimines. A small library of structurally and electronically modified chiral Lewis bases was considered; such compounds were shown to promote the enantioselective reduction of different substrates in good chemical yields. In the HSiCl3 addition to the model substrate N-phenylacetophenone imine, the organocatalyst of choice led to the formation of the corresponding amine with good stereoselectivity, up to 75% ee. Theoretical studies were also performed in order to elucidate the origin of the stereoselection.
研究了易于合成甚至商业可得的（S）-脯氨酸衍生物在三氯硅烷介导的酮亚胺还原反应中的行为。考虑了一组结构和电子修饰的手性路易斯碱的小库；这些化合物被证明可以以良好的化学收率促进不同底物的对映选择性还原。在模型底物 N-苯基苯乙酮亚胺的 HSiCl3 加成中，首选的有机催化剂导致相应胺的形成具有良好的立体选择性，最高可达 75%ee。还进行了理论研究，以阐明立体选择性的起源。
