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

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-arylat...

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Veröffentlicht in:	Journal of organic chemistry 2007-04, Vol.72 (8), p.3145-3148
Hauptverfasser:	Peng, Jinsong, Lin, Wenqing, Yuan, Shixue, Chen, Yuanwei
Format:	Artikel
Sprache:	eng
Schlagworte:	Catalysis Catalysts: preparations and properties Chemistry 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 Preparations and properties Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Zusammenfassung:	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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo0625958