Stereoselective intramolecular cyclization of γ-allylbenzamide via π–allylpalladium complex catalyzed by Pd(0)

• Published in: Tetrahedron Vol. 66; no. 12; pp. 2123 - 2131
• Main Authors: Pham, Van-Thoai, Joo, Jae-Eun, Lee, Kee-Young, Kim, Tai-Won, Mu, Yu, Ham, Won-Hun
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 20.03.2010; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Chiral building block; Chiral oxazine; Enantioselective catalysis; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Intramolecular cyclization; Organic chemistry; Palladium catalysis; Physical Sciences; Preparations and properties; Science & Technology; Intramolecular cyclization; Chiral oxazine; Enantioselective catalysis; Palladium catalysis; Chiral building block; INHIBITORS; STATINE; OXAZINE FORMATION; Intramolecular reaction; Protecting group; Catalytic reaction; Enantioselectivity; Tertiary phosphine; Palladium complex; Transition metal; Chiral compound; Oxazine derivatives; Allylic compound; Diastereoselectivity; Stereoselectivity; Cyclization; Sodium hydride; Benzenic compound; Benzamide derivatives; Secondary alcohol; Platinoid; Oxygen nitrogen heterocycle
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2010.01.075

An efficient procedure for synthesizing oxazines was developed by the palladium(0)-catalyzed intramolecular cyclization of a benzamide through a π-allylpalladium (II) complex. Interestingly, the diastereoselectivity of oxazine ring formation was dominantly controlled by the bulkiness of various protecting groups on the secondary alcohols. [Display omitted]