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Efficient Synthesis of Optically Active 2,3-Allenols via the Simple CuBr-Mediated Reaction of Optically Active Propargylic Alcohols with Paraformaldehyde

Shengming Ma*, Hairong Hou, Shimin Zhao, Guangwei Wang

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China, Email:

S. Ma, H. Hou, S. Zhao, G. Wang, Synthesis, 2002, 1643-1645.

DOI: 10.1055/s-2002-33656


Enantiomerically enriched 2,3-allenols were prepared by the CuBr-mediated homologation of the relatively easily available optically active terminal propargylic alcohols with paraformaldehyde in the presence of diisopropylamine.

see article for more examples

An Efficient Synthesis of Terminal Allenes from Terminal 1-Alkynes

J. Kuang, S. Ma, J. Org. Chem., 2009, 74, 1763-1765.

Key Words

propargylic alcohols, 2,3-allenols, allenes, copper

ID: J66-Y2002-1610