A C3‐Symmetric Amino Organocatalyst for Asymmetric Synthesis of Warfarin and Analogues: Mechanistic Insight from ESI‐MS Spectrometry and Computational Calculations

Abstract

A novel C3‐symmetric multi‐amino catalyst was synthesized and evaluated in the asymmetric Michael addition to produce warfarin and its analogues. The multi‐amino catalyst turned out to be efficient up to 1% molar without the use of acidic additives providing the desired product in 82% yield and maintaining good level of enantioselectivity. ESI‐MS experiments together with data supplied by theoretical models allowed us the understand the operating mechanism of the catalyst, clarifying the role of the amine functions and confirming the catalyst’s multifunctionality. The presence of three active catalytic sites makes it easy its anchoring to silica as solid support for applications in heterogeneous phase catalysis.