Palladium-Catalyzed Highly Stereoselective Synthesis of N-Aryl-3-arylmethylisoxazolidines via Tandem Arylation of O-Homoallylhydroxylamines

• Published in: Journal of organic chemistry Vol. 72; no. 8; pp. 3145 - 3148
• Main Authors: Peng, Jinsong, Lin, Wenqing, Yuan, Shixue, Chen, Yuanwei
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 13.04.2007; Amer Chemical Soc
• Subjects: Catalysis; Catalysts: preparations and properties; Chemistry; Chemistry, Organic; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; HALIDES; ORGANIC-SYNTHESIS; ALPHA-AMINO; DOMINO REACTIONS; 2,3-DIHYDROISOXAZOLES; ONE-POT SYNTHESIS; PD(II)-CATALYZED COUPLING-CYCLIZATION; EFFICIENT SYNTHESIS; ARYL; BETA-AMINO ALLENES; Arylation; Hydroxylamine; Catalytic reaction; Transition element complexes; Isoxazole derivatives; Ligand; Palladium complex; Tandem reaction; Diastereoselectivity; Stereoselectivity; Cyclization; Platinoid Complexes; Aromatic compound; Toluene derivatives; Chemical synthesis; Catalyst; Oxygen nitrogen heterocycle
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo0625958

The palladium-catalyzed tandem arylation of O-homoallylhydroxylamines with 2 equiv of aryl bromides was examined. With Pd2(dba)3 (1 mol %) as the catalyst, Xantphos (2 mol %) as the ligand, and NaOt-Bu as the base, the reactions of O-homoallylhydroxylamines with aryl bromides via sequential N-arylation/cyclization/C-arylation in toluene afforded the corresponding N-aryl-3-arylmethylisoxazolidines in good yields with excellent diastereoselectivity.