Carbene and Acid Cooperative Catalytic Reactions of Aldehydes and o-Hydroxybenzhydryl Amines for Highly Enantioselective Access to Dihydrocoumarins

• المؤلفون الرئيسيون: Chen, Xingkuan, Song, Runjiang, Liu, Yingguo, Ooi, Chong Yih, Jin, Zhichao, Zhu, Tingshun, Wang, Hongling, Hao, Lin, Chi, Robin Yonggui
• مؤلفون آخرون: School of Physical and Mathematical Sciences
• التنسيق: مقال
• اللغة: English
• منشور في: 2018
• الموضوعات: Dihydrocoumarins; Enantioselective
• الوصول للمادة أونلاين: https://hdl.handle.net/10356/88490; http://hdl.handle.net/10220/44659

A highly enantioselective method for quick access to dihydrocoumarins is reported. The reaction involves a cooperative catalytic process with carbene and in situ generated Brønsted acid as the catalysts. α-Chloro aldehyde and readily available and stable o-hydroxybenzhydryl amine substrates were used to generate reactive azolium ester enolate and ortho-quinone methide (o-QM) intermediates, respectively, to form dihydrocoumarins with exceptionally high diastereo- and enantioselectivities. The catalytic reaction products can be easily transformed to valuable pharmaceuticals and bioactive molecules.