… from oximes. Tandem michael addition-1, 3-dipolar cycloaddition reactions. class 2 processes utilising bifunctional michael acceptor-dipolarophile components.

…, F Heaney, JF Malone, S Rajviroongit, V Sridharan…

Index: Grigg, Ronald; Dorrity, Michael J.; Heaney, Frances; Malone, John F.; Rajviroongit, Shuleewan; Sridharan, Visuvanathar; Surendrakumar, Sivagnanasundram Tetrahedron, 1991 , vol. 47, # 38 p. 8297 - 8322

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Citation Number: 54

Abstract

Aldoximes and ketoximes react with a range of bifunctional Michael acceptor-dipolarophile substrates comprising functionalised 1, 3-, 1, 4-and 1, 5-dienes via a tandem process involving an N-alkenyl nitrone intermediate. The 1, 3-dienes react regio-and stereo- specifically to give 1-aza-7-oxabicyclo [2.2. 1] heptanes whilst sterically unencumbered aryl aldoximes and 1, 4-dienes give 1-aza-2-oxabicyclo [3.2. 1] octane derivatives. Ketoximes ...