Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
Henan Engineering Laboratory of Green Synthesis for Pharmaceuticals, College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, 476000, China.
Angew Chem Int Ed Engl. 2023 May 15;62(21):e202301126. doi: 10.1002/anie.202301126. Epub 2023 Apr 18.
N-heterocyclic carbene (NHC)-catalyzed enantioselective Mannich-type reactions of the biomass-derived platform compound 5-(chloromethyl)furfural (CMF) with imines were developed. A series of high-value-added chiral amines were afforded in good to high yields with excellent regio- and enantioselectivities. The bifunctional NHC derived from ʟ-pyroglutamic acid efficiently steered the remote addition of the trienolate intermediate to the imine in a highly stereocontrolled manner. This represents the first enantioselective reaction proceeding via an NHC-bound trienolate intermediate.
N-杂环卡宾（NHC）催化生物质衍生平台化合物 5-（氯甲基）糠醛（CMF）与亚胺的对映选择性 Mannich 型反应得到了发展。一系列高附加值的手性胺以良好到高产率和优异的区域和对映选择性得到了。来源于 L-焦谷氨酸的双功能 NHC 有效地以高度立体控制的方式引导三烯醇化物中间体对亚胺的远程加成。这代表了首例通过 NHC 键合的三烯醇化物中间体进行的对映选择性反应。
