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

作者：Zhi‐Hong Du, Bao‐Xiu Tao, Meng Yuan, Wen‐Juan Qin, Yanli Xü, Pei Wang, Chao‐Shan Da · 发表于：Organic Letters · 年份：2020 · DOI：10.1021/acs.orglett.0c01407 · 被引用次数：27 · 研究领域：Asymmetric Synthesis and Catalysis、Chemical Synthesis and Analysis、Synthetic Organic Chemistry Methods

β-Turn tetrapeptides were demonstrated to catalyze asymmetric aldol reaction of α-branched aldehydes and α-carbonyl aldehydes, i.e. glyoxylates and α-ketoaldehydes, to biomimetically synthesize acyclic all-carbon quaternary center-bearing 1,4-dicarbonyls in high yield and excellent enantioselectivity under mild conditions. The spatially restricted environment of the tetrapeptide warrants high enantioselectivity and yield with broad substrates. Using this protocol, ( R )-pantolactone, the key intermediate of vitamin B5, was readily accessed in a practical, efficient, and environmentally benign process from inexpensive starting materials.