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Updated: Sep 3, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Diastereoselective Addition of Racemic α-Boryl Organozinc Reagents to Aldimines
Shuda Luo1,2, Xin An1,2, Yuanhang Bai1,2
1School of Life Science and Technology, Northwestern Polytechnical University, Xi'an710072, China.
Abstract:
The addition of alkylzinc reagents to imines is a key route to amines, but suffers from poor selectivity when racemic secondary alkylzincs are employed. Herein, we report a transition-metal-free diastereoselective addition of racemic α-boryl organozincs to aldimines, affording anti-β-aminoborons with good to excellent diastereoselectivities. Furthermore, Cu-catalyzed addition of racemic α-boryl organozincs to N-tert-butanesulfinyl aldimines afforded enantioenriched anti-β-aminoborons, preferentially delivering one of the four possible stereoisomers with high selectivity.
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