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Enantioselective Synthesis of 2‑Substitued-Tetrahydroisoquinolin-1-yl Glycine Derivatives via Oxidative Cross-Dehydrogenative Coupling of Tertiary Amines and Chiral Nickel(II) Glycinate
journal contribution
posted on 2013-11-15, 00:00 authored by Shengbin Zhou, Jiang Wang, Daizong Lin, Fei Zhao, Hong LiuThe
asymmetric synthesis of 2-substituted-tetrahydroisoquinolin-1-yl
glycines was achieved by an oxidative cross-dehydrogenative coupling
(CDC) reaction. This method for activation of the α-C-H bonds
of amines with chiral nickel(II) glycinate using o-chloranil as the sole oxidant afforded highly diastereoselective
coupling adducts. The decomposition of coupling adducts readily afforded
2-substituted-tetrahydroisoquinolin-1-yl glycine derivatives.