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Synfacts 2011(11): 1244-1244  
DOI: 10.1055/s-0031-1289259
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

α-Alkylation of Aldehydes by Oxidative Coupling with Molecular Oxygen

Contributor(s): Benjamin List, Olga Lifchits
B. Zhang, S.-K. Xiang, L.-H. Zhang, Y. Cui, N. Jiao*
Peking University, Beijing and East China Normal University, Shanghai, P. R. of China
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Publication History

Publication Date:
19 October 2011 (online)

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Significance

Cui, Jiao, and colleagues report an SN1-type α-alkylation of aldehydes, which uses a combination of dehydrogenative C-H activation and asymmetric enamine catalysis. The authors used molecular oxygen under acid catalysis to oxidize heterocycles 1 to stable benzylic cationic species. At the same time, MacMillan catalyst 4 was used to activate the aldehyde component 2 as an enamine for the coupling. A range of aliphatic and aromatic aldehydes 2 could be alkylated with good to excellent yields and enantioselectivities.