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Synfacts 2010(5): 0603-0603  
DOI: 10.1055/s-0029-1219756
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

NHC-Catalyzed Cycloaddition of Ketenes and 9,10-Phenanthrenequinone

Contributor(s): Benjamin List, Olga Lifchits
P.-L. Shao, X.-Y. Chen, L.-H. Sun, S. Ye*
Beijing National Laboratory for Molecular Sciences, P. R. of China
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Publication History

Publication Date:
22 April 2010 (online)

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Significance

Ye and colleagues report an enan­tioselective [4+2] cycloaddition between ketenes 1 and 9,10-phenanthrenequinone (2) catalyzed by N-heterocyclic carbene 3. 9,10-Phenanthrenequinone proved to be most amenable to catalysis due to its lower reactivity compared to other ortho-quinones. Based on the work of Lectka and colleagues (J. Am. Chem. Soc. 2006, 128, 1810) products 4 can be potentially derivatized to chiral α-hydroxy esters by a transesterification-oxidative cleavage sequence (see Scheme).