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Enantioselective Iridium-Catalyzed Hydrogenation of 1- and 3-Substituted Isoquinolinium Salts

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  • Financial support from the National Natural Science Foundation of China (21202162 and 21125208) and the National Basic Research Program of China (2010CB833300) is acknowledged.

Abstract

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Asymmetric hydrogenation: The title reaction provides an efficient and rapid access to chiral 1- and 3-substituted 1,2,3,4-tetrahydroisoquinolines with excellent enantioselectivity (see scheme; L=ligand). A preliminary mechanistic study indicates that the 1,2-hydride addition might be the initial step in the reaction. The method has been used in the synthesis of urinary antispasmodic drug (+)-solifenacin.

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