Enantioselective Synthesis of Carbo- and Heterocycles Through a CuH-Catalyzed Hydroalkylation Approach

Y. - M. Wang, Bruno, N. C. , Placeres, Á. L. , Zhu, S. , and Buchwald, S. L. “Enantioselective Synthesis of Carbo- and Heterocycles Through a CuH-Catalyzed Hydroalkylation Approach”, J. Am. Chem. Soc., 2015, 137(33), 10524–10527.

Abstract:

The enantioselective, intramolecular hydroalkylation of halide-tethered styrenes has been achieved through a copper hydride-catalyzed process. This approach allowed for the synthesis of enantioenriched cyclobutanes, cyclopentanes, indanes, and six-membered N- and O-heterocycles. This protocol was applied to the synthesis of the commercial serotonin reuptake inhibitor (?)-paroxetine.The enantioselective, intramolecular hydroalkylation of halide-tethered styrenes has been achieved through a copper hydride-catalyzed process. This approach allowed for the synthesis of enantioenriched cyclobutanes, cyclopentanes, indanes, and six-membered N- and O-heterocycles. This protocol was applied to the synthesis of the commercial serotonin reuptake inhibitor (?)-paroxetine.

Authors

Yiming Wang, Shaolin Zhu, Nick Bruno, Angel L. Placeres