Synfacts 2009(7): 0794-0794  
DOI: 10.1055/s-0029-1217307
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Asymmetric Synthesis of Allenoates by Isomerization of Alkynoates

Contributor(s): Benjamin List, Steffen Müller
H. Liu, D. Leow, K.-W. Huang*, C.-H. Tan*
National University of Singapore, Singapore
Further Information

Publication History

Publication Date:
22 June 2009 (online)


The authors report an enantio­selective isomerization of various alkynoates to the corresponding allenoates catalyzed by a chiral Brønsted base. The products were obtained in moderate to high yields and good enantioselectivities at relatively low catalyst loadings. Although most of the products were inseparable from un­reacted starting material, the obtained mixtures were successfully used in further transformations, such as cycloadditions or lactonizations. These reactions proceeded with good chirality transfer and allowed the reisolation of the unreacted alkyne.