The Journal of organic chemistry

Cyclization-Cycloaddition Cascade of Rhodium Carbenoids Using Different Carbonyl Groups. Highlighting the Position of Interaction

A Padwa, ZJ Zhang, L Zhi

Index: Padwa, Albert; Zhang, Zhijia J.; Zhi, Lin Journal of Organic Chemistry, 2000 , vol. 65, # 17 p. 5223 - 5232

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Citation Number: 37

Abstract

A series of 3-diazoalkanediones, when treated with a catalytic quantity of a rhodium (II) carboxylate, were found to afford oxabicyclic dipolar cycloadducts derived by the trapping of a carbonyl ylide intermediate. The reaction involves generation of the 1, 3-dipole by intramolecular cyclization of the keto carbenoid onto the oxygen atom of the neighboring keto group. Both five-and six-ring carbonyl ylides are formed with the same efficiency. A ...