A reaction intermediate is a key molecular entity that has been used in explaining how starting materials converts into the final products in the reaction, and it is usually unstable, highly reactive, and short-lived. Extensive efforts have been devoted in identifying and characterizing such species via advanced physico-chemical analytical techniques. As an appealing alternative, trapping experiments are powerful tools in this field. This trapping strategy opens an opportunity to discover multicomponent reactions. In this work, we report various highly diastereoselective and enantioselective four-component reactions (containing alcohols, diazoesters, enamines/indoles and aldehydes) which involve the coupling of in situ generated intermediates (iminium and enol). The reaction conditions presented herein to produce over 100 examples of four-component reaction products proceed under mild reaction conditions and show high functional group tolerance to a broad range of substrates. Based on experimental and computational analyses, a plausible mechanism of this multicomponent reaction is proposed.

反应中间体是一个关键的分子实体，已被用于解释起始原料如何在反应中转化为最终产物，它通常不稳定、反应性高且寿命短。通过先进的物理化学分析技术，人们付出了广泛的努力来识别和表征这些物种。作为一个有吸引力的替代方案，诱捕实验是该领域的强大工具。这种捕获策略为发现多组分反应提供了机会。在这项工作中，我们报告了各种高度非对映选择性和对映选择性四组分反应（包含醇、重氮酯、烯胺/吲哚和醛），这些反应涉及原位生成的中间体（亚胺和烯醇）的偶联。本文介绍的反应条件可产生 100 多个四组分反应产物的实例，这些反应产物在温和的反应条件下进行，并显示出对各种底物的高官能团耐受性。基于实验和计算分析，提出了这种多组分反应的可能机理。