Desymmetrization of 1,3-Diones by Catalytic Enantioselective Condensation with Hydrazine

• DOI: 10.1021/jacs.1c01366
• Publication Date: 2021-03-16T13:57:01Z
• Authors: Binmiao Yang; Jun Dai; Yixin Luo; Kai Kiat Lau; Yu Lan; Zhihui Shao; Yu Zhao
• Keywords: 01 natural sciences; 0104 chemical sciences

We present herein an unprecedented desymmetrization of meso 1,3-diones by enantioselective intermolecular condensation. Under the catalysis by a chiral phosphoric acid, a range of readily available 1,3-diones undergo reaction with hydrazines to produce cyclic and acyclic keto-hydrazones bearing an all-carbon quaternary center in high efficiency and enantioselectivity. These compounds are also highly versatile for the preparation of multifunctional building blocks and heterocycles in excellent stereoselectivity.