Bifunctional N-Heterocyclic Carbenes Derived from l-Pyroglutamic Acid and Their Applications in Enantioselective Organocatalysis

Accounts of Chemical Research
Xiang-Yu ChenSong Ye

Abstract

ConspectusIn nature, enzymes are a powerful medium for the construction of enantiomerically pure chemicals, which always inspires synthetic chemists to explore new catalysts to imitate the enzyme machinery for asymmetric transformations. Vitamin B1, a bifunctional thiazolium N-heterocyclic carbene (NHC) precursor, is the coenzyme for transketolase. In the past two decades, a series of chiral NHCs, including monocyclic, bicyclic, tetracyclic, and even bridged ones, have been synthesized and successfully utilized as efficient organocatalysts for a wide variety of asymmetric organic reactions. The utility of bifunctional catalysts can enhance catalytic activity and improve stereochemical control through their synchronous activation of both reaction partners. However, the NHCs possessing multiple activation sites are far less developed.This Account gives an overview of our research on the design, development, and applications of bifunctional NHCs in organocatalysis. We synthesized a series of l-pyroglutamic acid-derived bifunctional NHCs bearing a free hydroxyl group which can interact with carbonyl or imino groups via hydrogen-bonding. Further studies revealed that these bifunctional catalysts worked well for a variety of reaction...Continue Reading

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Jun 10, 2020·Organic & Biomolecular Chemistry·Jasneet KaurSwapandeep Singh Chimni
Jul 1, 2020·Chemical Communications : Chem Comm·Tamal Kanti Das, Akkattu T Biju
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Oct 10, 2020·Chemistry : a European Journal·Qing-Zhu LiJun-Long Li
Mar 25, 2021·Journal of the American Chemical Society·Kun Liu, Armido Studer
Apr 20, 2021·Advanced Healthcare Materials·Qian-Ni YeJun Wang
May 6, 2021·Organic & Biomolecular Chemistry·Yuanyuan HuBingwei Zhou
Apr 9, 2021·Chemistry : a European Journal·Guanzhao WuGuigen Li
Jun 8, 2021·Chemical Science·Jing LiuWen-Jing Xiao
Jun 15, 2021·Chemical Science·Xiaolin PengZhichao Jin
Jun 25, 2021·Chemical Science·Runjiang SongYonggui Robin Chi

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