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Synfacts 2005(3): 0341-0341  
DOI: 10.1055/s-2005-921648
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Thiourea-Catalyzed Acyl-Mannich Reactions of Isoquinolines

Contributor(s): Benjamin List, Sebastian Hoffmann
M. S. Taylor, N. Tokunaga, E. N. Jacobsen*
Harvard University, Cambridge, USA
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Publication History

Publication Date:
22 November 2005 (online)

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Significance

An organocatalyzed asymmetric addition of carbon-centered nucleophiles to aromatic nitrogen heterocycles is described. A thiourea catalyst allows the addition of ketene acetals to isoquinolines in good yields and up to 92% ee (8 examples, 10 mol% catalyst, -78 °C).