Tetrahedron

Ether-directed palladium (II)-catalysed aza-Claisen rearrangements: studies on the origin of the directing effect

AG Jamieson, A Sutherland

Index: Jamieson, Andrew G.; Sutherland, Andrew Tetrahedron, 2007 , vol. 63, # 10 p. 2123 - 2131

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Citation Number: 29

Abstract

Four new chiral δ-substituted allylic trichloroacetimidates have been synthesised to probe the origin of the high diastereoselectivity observed for the MOM-ether directed palladium (II)- catalysed aza-Claisen rearrangement. Rearrangement of these compounds has not only provided strong evidence for this directing effect but also that during the rearrangement both oxygen atoms from the MOM-ether are involved in coordinating to and directing the ...

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