Ligand-Enabled β-C(sp3)-H Lactamization of Tosyl-Protected Aliphatic Amides Using a Practical Oxidant

被引：25
作者：
Zhuang, Zhe [1 ]
Liu, Shuang [1 ]
Cheng, Jin-Tang [1 ]
Yeung, Kap-Sun [2 ]
Qiao, Jennifer X. [3 ]
Meanwell, Nicholas A. [3 ]
Yu, Jin-Quan [1 ]
机构：
[1] Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
[2] Bristol Myers Squibb Res & Early Dev, Small Mol Drug Discovery, 100 Binney St, Cambridge, MA 02142 USA
[3] Bristol Myers Squibb Res & Early Dev, Small Mol Drug Discovery, POB 4000, Princeton, NJ 08543 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2022年 / 61卷 / 34期
关键词：
C-H Activation; Carboxylic Acids; Lactamization; Ligand Design; Palladium; C(SP(3))-H BOND ACTIVATION; AMINO-BETA-LACTAMS; STEREOSELECTIVE-SYNTHESIS; SEQUENTIAL MONOARYLATION/AMIDATION; INTRAMOLECULAR C(SP(3))-H; INTERMOLECULAR AMINATION; OXIDATIVE CYCLIZATION; AMIDATION; ACETOXYLATION; CARBONYLATION;
D O I：
10.1002/anie.202207354
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The development of C(sp(3))-H functionalization reactions that use common protecting groups and practical oxidants remains a significant challenge. Herein we report a monoprotected aminoethyl thioether (MPAThio) ligand-enabled beta-C(sp(3))-H lactamization of tosyl-protected aliphatic amides using tert-butyl hydrogen peroxide (TBHP) as the sole oxidant. This protocol features exceedingly mild reaction conditions, reliable scalability, and the use of practical oxidants and protecting groups. Further derivatization of the beta-lactam products enables the synthesis of a range of biologically important motifs including beta-amino acids, gamma-amino alcohols, and azetidines.
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页数：5
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