X=Y–ZH system as potential 1,3-dipoles. Part 59: Cascade 1,3-azaprotio cyclotransfer–1,3-dipolar cycloaddition (1,3-APT–1,3-DC) reactions of benzobicyclo[3.3.1]non-5-en-9-one oxime

• Published in: Tetrahedron Vol. 59; no. 50; pp. 9997 - 10007
• Main Authors: Dondas, H.Ali, Fishwick, Colin W.G, Grigg, Ronald, Thornton-Pett, Mark
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 08.12.2003; Elsevier
• Subjects: 1,3-azaprotio cyclotransfer; 1,3-dipolar cycloaddition; anorectic and antidepressant; benzobicyclo; Chemistry; Chemistry, Organic; nitrone; oxime; Physical Sciences; Science & Technology; spiro-oxazolidines; 1,3-azaprotio cyclotransfer; spiro-oxazolidines; anorectic and antidepressant; oxime; benzobicyclo; nitrone; 1,3-dipolar cycloaddition; NITRONES; MULTIPLICATION; DIVINYL KETONE; KETOXIMES; DIPOLAROPHILES; CYCLOADDUCTS; RATE ENHANCEMENT; GENERATION; CHIRALITY; ALDOXIMES
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2003.10.027

Preparation of some novel spiro-oxazolidines related to 3 , which is known to posses anorectic and antidepressant activity, via 1,3-APT–1,3-DC cascades of the oxime of benzobicyclo[3.3.1]non-5-en-9-one 1 is described. Substrate 1 allows the influence of the two bridges on the cascade to be assessed with respect to the configuration of the nitrone that is generated and the facial selectivity of the subsequent cycloaddition. Graphic