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Synfacts 2009(11): 1271-1271  
DOI: 10.1055/s-0029-1218103
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Lappaconitine Catalysis

Contributor(s): Benjamin List, Saihu Liao
B. Gong, Q. Meng*, T. Su, M. Lian, Q. Wang, Z. Gao
Dalian University of Technology, P. R. of China
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Publication History

Publication Date:
22 October 2009 (online)

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Significance

Three commercially available terpenoid alkaloids were evaluated as Brønsted base catalysts for the α-hydroxylation of β-keto esters. ­Lappaconitine was found effective for this transformation when using t-BuOOH as the oxidant, ­affording the hydroxylation products in 53-95% yield with moderate to good enantioselectivity (er up to 92.5:7.5).