Tetrahedron

Chemo-and diastereoselective cyclopropanation of allylic amines and carbamates

…, SG Davies, JA Lee, KB Ling, PM Roberts, AJ Russell…

Index: Csatayova, Kristina; Davies, Stephen G.; Lee, James A.; Ling, Kenneth B.; Roberts, Paul M.; Russell, Angela J.; Thomson, James E. Tetrahedron, 2010 , vol. 66, # 43 p. 8420 - 8440

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Citation Number: 21

Abstract

A highly chemo-and diastereoselective protocol for the cyclopropanation of tertiary allylic amines with Shi's carbenoid [CF3CO2ZnCH2I] is described. The high levels of diastereoselectivity observed in these reactions may be attributed to chelation of the nitrogen atom to the zinc reagent, which then transfers a methylene unit to the syn-face of the olefin. Furthermore, a stereodivergent protocol for the cyclopropanation of a range of ...