Journal of the American Chemical Society

Non-carbonyl-stabilized metallocarbenoids in synthesis: the development of a tandem rhodium-catalyzed bamford-stevens/thermal aliphatic claisen rearrangement …

JA May, BM Stoltz

Index: May, Jeremy A.; Stoltz, Brian M. Journal of the American Chemical Society, 2002 , vol. 124, # 42 p. 12426 - 12427

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Citation Number: 66

Abstract

A tandem rhodium-catalyzed Bamford-Stevens/Claisen rearrangement is presented. The tandem reaction uses Eschenmoser hydrazones for the in situ generation of non-carbonyl- stabilized diazo alkanes, which are presumably intercepted by Rh (II) catalysts to induce a 1, 2-hydride migration. This sequence provides high levels of stereocontrol for the generation of simple acyclic (Z)-enol ethers. These enol ethers undergo either thermal or Lewis acid ...