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Peptide-Catalyzed Highly Asymmetric Cross-Aldol Reaction of Aldehydes to Biomimetically Synthesize 1,4-Dicarbonyls

Zhi-Hong Du, Bao-Xiu Tao, Meng Yuan, Wen-Juan Qin, Yan-Li Xu, Pei Wang and Chao-Shan Da*

*Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou 730000, China, Email:

Z.-H. Du, B.-X. Tao, M. Yuan, W.-J. Qin, Y.-L. Xu, P. Wang, C.-S. Da, Org. Lett., 2020, 22, 4444-4450.

DOI: 10.1021/acs.orglett.0c01407 (free Supporting Information)

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β-Turn tetrapeptides catalyze asymmetric aldol reactions of α-branched aldehydes and α-carbonyl aldehydes, i.e. glyoxylates and α-ketoaldehydes, to provide acyclic all-carbon quaternary center-bearing 1,4-dicarbonyls in high yield and excellent enantioselectivity under mild conditions.

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Key Words

aldol reaction, organocatalysis

ID: J54-Y2020