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Asymmetric α-Allylation of Aldehydes with Alkynes by Integrating Chiral Hydridopalladium and Enamine Catalysis

Yong-Liang Su, Lu-Lu Li, Xiao-Le Zhou, Zhen-Yao Dai, Pu-Sheng Wang* and Liu-Zhu Gong*

*Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China, Email: pusherustc.edu.cn, gonglzustc.edu.cn

Y.-L. Su, L-L. Li, X.-L. Zhou, Z.-Y. Dai, P.-S. Wang, L.-Z. Gong, Org. Lett., 2018, 20, 2403-2406.

DOI: 10.1021/acs.orglett.8b00740 (free Supporting Information)


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Abstract

A combination of chiral hydridopalladium and enamine catalysis enables an asymmetric α-allylation of aldehydes with alkynes. The ternary catalyst system, consisting of an achiral palladium complex, a primary amine, and a chiral phosphoric acid tolerates a wide scope of α,α-disubstituted aldehydes and alkynes and provides the corresponding allylation products in high yields and with excellent levels of enantioselectivity.

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Key Words

α-allylation of carbonyl compounds, 1,3-dienes


ID: J54-Y2018