• Organocatalytic Enantioselective Synthesis of 1,3-Disubstituted Allenols

     

Organocatalytic Enantioselective Synthesis of 1,3-Disubstituted Allenols

Dimethylprolinol Versus Diphenylprolinol in CuBr2-Catalyzed Enantioselective Allenylation of Terminal Alkynols: D. Ma, X. Duan, C. Fu, X. Huang, S. Ma
Synthesis 2018, DOI: 10.1055/s-0036-1592007


Axially stereogenic allenes are important compounds in organic chemistry both for their usefulness as synthetic intermediates and because several natural substances belong to this family of cumulene derivatives. Recently, the group of Professor Shengming Ma at Zhejiang University (P. R. of China) reported a versatile organocatalyzed process for accessing 1,3-disubstituted allenes with a high degree of enantiocontrol.

  • Synthesis of 1,3-Disubstituted Allenols

     
Professor Ma said: “The CuBr2-catalyzed EATA (Enantioselective Allenylation of Terminal Alkynes) reaction of terminal alkynols and aldehydes in the presence of (R)- or (S)-dimethylprolinol easily provides chiral allenols in high ee, which may be transferred to other types of chiral allenes bearing versatile functionalities such as aldehydes, esters, amides, amines, halides, malonates, etc.”
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