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Synlett 2011(10): 1423-1426  
DOI: 10.1055/s-0030-1260565
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Nickel-Promoted Carboxylation/Cyclization Cascade of Allenyl Aldehyde under an Atmosphere of CO2

Masanori Takimoto, Mitsunobu Kawamura, Miwako Mori, Yoshihiro Sato*
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
e-Mail: biyo@pharm.hokudai.ac.jp;
Further Information

Publication History

Received 10 February 2011
Publication Date:
16 May 2011 (online)

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Abstract

In the presence of a stoichiometric amount of Ni(0) complex, allenyl aldehydes smoothly reacted with carbon dioxide at an ambient temperature and pressure in a regioselective manner. The reaction involves an intramolecular cyclization of aldehyde and ­allene moieties to afford cyclic carboxylic acid derivatives having a hydroxyl group.

Key words

allenes - aldehydes - carboxylic acid - cyclization - nickel

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1

Present address: Organometallic Chemistry Laboratory, RIKEN Advanced Science Institute, Hirosawa 2-1, Wako, Saitama 351-0198, Japan.

9

Oxidation of the mixture of trans- and cis-3a afforded the corresponding ketone as the sole product in high yield.