Article

Catalytic asymmetric synthesis of optically active allenes from terminal alkynes.

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, PR China.
Organic Letters (impact factor: 5.86). 03/2012; 14(5):1346-9. DOI:10.1021/ol300296k pp.1346-9
Source: PubMed

ABSTRACT CuBr and ZnI(2) have been developed as catalysts or subcatalysts for the efficient asymmetric synthesis of axially chiral allenols with up to 97% ee from readily available propargylic alcohols, aliphatic or aromatic aldehyde, pyrrolidine, and commerically available ligands. The alcohol unit in the terminal alkynes plays a very important role for ensuring high enantioselectivity via coordination.

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Keywords

alcohol unit
 
aromatic aldehyde
 
available propargylic alcohols
 
axially chiral allenols
 
commerically available ligands
 
efficient asymmetric synthesis
 
enantioselectivity
 

Juntao Ye