Enantioselective synthesis of α-amino ketones through palladium-catalyzed asymmetric arylation of α-keto imines. Issue 13 (10th March 2022)

• Record Type: Journal Article
• Authors: Wen, Wei; Ai, Zhao-Pin; Yang, Chang-Lin; Li, Chao-Xing; Wu, Zhu-Lian; Cai, Tian; Guo, Qi-Xiang
• Is Part Of: Chemical science. Volume 13:Issue 13(2022)
• Page Start: 3796
• Page End: 3802
• Publication Date: 2022-03-10
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2sc00386d
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Chiral α-amino ketones are common structural motifs in natural products and pharmaceuticals, as well as important synthons in organic synthesis. Abstract : Chiral α-amino ketones are common structural motifs in natural products and pharmaceuticals, as well as important synthons in organic synthesis. Thus, establishing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein we disclose a new catalytic asymmetric approach for the synthesis of chiral α-amino ketones through a chiral palladium-catalyzed arylation reaction of in situ generated challenging α-keto imines from previously unreported C -acyl N -sulfonyl- N, O -aminals, with arylboronic acids. The current reaction offers a straightforward approach to the asymmetric synthesis of acyclic α-amino ketones in a practical and highly stereocontrolled manner. Meanwhile, the multiple roles of the chiral Pd(ii ) complex catalyst in the reaction were also reported.