title: Stereoselective synthesis of chiral α-amino-β-lactams through palladium(II)-catalyzed sequential monoarylation/amidation of C(sp(3) )-H bonds.
abstract: Give Me an Ar, give Me an N! Arylation of the methyl group in a simple derivative of readily available alanine under palladium catalysis was followed by intramolecular amidation at the same position to give chiral α-amino-β-lactams with a wide range of aryl substituents (see scheme; Phth=phthaloyl). The α-amino-β-lactams were obtained in moderate to high yields with good functional-group tolerance and high diastereoselectivity.
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou 310027 (China) http://mypage.zju.edu.cn/bfshi.
authors.forename: Qi
authors.initials: Q
authors.lastname: Zhang
authors.forename: Kai
authors.initials: K
authors.lastname: Chen
authors.forename: Weihao
authors.initials: W
authors.lastname: Rao
authors.forename: Yuejun
authors.initials: Y
authors.lastname: Zhang
authors.forename: Fa-Jie
authors.initials: FJ
authors.lastname: Chen
authors.forename: Bing-Feng
authors.initials: BF
authors.lastname: Shi
mesh_terms: D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D047090:beta-Lactams; D010165:Palladium
keywords: CH activation; amidation; arylation; palladium; β-lactams