Studies in 3-oxy-assisted 3-aza Cope rearrangements

MJS Gomes, L Sharma, S Prabhakar…

Index: Gomes, Mario J. S.; Sharma, Lalit; Prabhakar, Sundaresan; Lobo, Ana M.; Gloria, Paulo M. C. Chemical Communications, 2002 , # 7 p. 746 - 747

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Citation Number: 6

Abstract

Examination of the Table shows that the reactions occur in consistently good yield to provide the oxime ethers 2d as a mixture of the syn and anti isomers. Under virtually identical experimental conditions the cyclohexyl enamines 1b (R = cyclohexyl; R 1 = R 2 = R 3 = R 4 = H; R 5 = SO 2 Tol or R 1 = R 2 = R 3 = R 4 = H; R 5 = CO 2 Me) showed no tendency to undergo the aza-Cope reaction, underlining the importance of the silyloxy group in promoting the rearrangement.