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New Strategy for the Synthesis of Axially Chiral Allenic Compounds
Date:2022-11-29 

Recently, a  Chinese research team led by Prof. GUO Chang at the University of Science and  Technology of China (USTC) of the Chinese Academy of Sciences (CAS) managed to  catalyze asymmetric propargyl substitution reaction with nickel-derived  catalyst,  successfully synthesizing a series of chiral  dienes in a diversified route. Their work was published in Nature  Communications and Journal  of the American Chemical Society.


Due to  their unique structural characteristics, allenic compounds have been widely used  in synthetic chemistry, pharmaceutical chemistry and material science. They also  function as important structures in a wide range of efficient construction of  various bioactive molecules. The development of efficient and highly selective  synthesis methods to construct novel chiral allenic compounds has been a  research focus.


The  researchers managed to realize the diversified phosphonylation of racemic  propargyl carbonate and synthesized a series of tertiary phosphine oxides  effectively by applying two different ligands. One is to synthesize  functionalized phosphinoyl 1,3-butadienes with the ligand dcybpz. While the  other one is realizing the construction of versatile chiral allenylphosphoryl  derivatives with high enantiopurity by applying the newly developed BDPP-type  ligand.


Additionally, the team designed a  series of N-sulfonyl hydrazide reagents,  which were used in the nickel catalyzed asymmetric propargyl substitution/Myers  rearrangement tandem reaction, achieving a high stereoselectivity in the  synthesis of 1,3-disubstituted allenic compounds. This powerful strategy can be  applied in the synthesis of natural  allenic  compounds, indicating its  great  potential.


(Written by WANG Yiheng, edited by TONG Xinyang, USTC News Center)

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