手性大位阻三组分Lewis酸碱催化的不对称二硫化反应
Catalytic Asymmetric Disulfuration by a Chiral Bulky Three-Component Lewis Acid-Base.
作者信息
Zhang Qi, Li Yao, Zhang Long, Luo Sanzhong
机构信息
Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
Department of Chemistry, University of Chinese Academy of Sciences, Beijing, 100490, China.
出版信息
Angew Chem Int Ed Engl. 2021 May 3;60(19):10971-10976. doi: 10.1002/anie.202101569. Epub 2021 Apr 6.
A three-component Lewis acid-base (Lewis trio) involving a bulky chiral primary amine, B(C F ) and a bulky tertiary amine has been developed as an effective enamine catalyst for enantioselective disulfuration reactions. The bulky tertiary amine was found to activate a bulky primary-tertiary diamine-borane Lewis pair for enamine catalysis via frustrated interaction. The resulted chiral bulky Lewis trio (BLT) allows for the construction of chiral disulfides via direct disulfuration with β-ketocarbonyls or α-branched aldehydes in a practical and highly stereocontrolled manner.
一种由大位阻手性伯胺、B(CF) 和大位阻叔胺组成的三组分路易斯酸碱（路易斯三元组）已被开发为用于对映选择性二硫化反应的有效烯胺催化剂。发现大位阻叔胺通过受阻相互作用活化大位阻伯-叔二胺-硼烷路易斯对以进行烯胺催化。所得的手性大位阻路易斯三元组（BLT）能够通过与β-酮羰基化合物或α-支链醛直接二硫化，以实用且高度立体可控的方式构建手性二硫化物。
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