Tetrahedron Letters

Dearomative radical spirocyclization from N-ce: raghubenzyltrichloroacetamides revisited using a copper (I)-mediated atom transfer reaction leading to 2-azaspiro [4.5 …

F Diaba, JA Montiel, A Martínez-Laporta, J Bonjoch

Index: Diaba, Faiza; Montiel, Juan A.; Martinez-Laporta, Agustin; Bonjoch, Josep Tetrahedron Letters, 2013 , vol. 54, # 21 p. 2619 - 2622

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Citation Number: 5

Abstract

An atom transfer radical dearomatizing spirocyclization from N-benzyltrichloroacetamides using CuCl regioselectively leads to 2-azaspiro [4.5] decadienes, in which the labile allylic chlorine atom is easily replaced by a hydroxyl group in aqueous medium or by quenching with methanol or allylamine. After oxidation of the target compound, the N-tert-butyl group can be removed from the resulting spirocyclohexanedienone.

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