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Ge, Yao; Han, Zhaobin; Wang, Zheng; Feng, Chen‐Guo; Zhao, Qian; Lin, Guo‐Qiang; Ding, Kuiling
Angewandte Chemie International Edition, October 1, 2018, Volume: 57, Issue: 40Journal Article
The first asymmetric hydrogenation of 3‐ylidenephthalides has been developed using the IrI complex of a spiro4,4‐1,6‐nonadiene‐based phosphine‐oxazoline ligand (SpinPHOX) as the catalyst, affording a wide variety of chiral 3‐substituted phthalides in excellent enantiomeric excesses (up to 98 % ee). The utility of the protocol has been demonstrated in the asymmetric synthesis of chiral drugs NBP and BZP precursor, as well as the natural products chuangxinol and typhaphthalide. A shortcut to a wide variety of chiral 3‐substituted phthalides with pharmacological interests has been realized by SpinPHOX/Ir catalyzed asymmetric hydrogenation of 3‐ylidenephthalides in high enantioselectivities (up to 98 % ee).
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