Cyclic nitriles: Diastereoselective alkylations

FF Fleming, S Gudipati, Z Zhang, W Liu…

Index: Fleming, Fraser F.; Zhang, Zhiyu; Liu, Wang; Knochel, Paul Journal of Organic Chemistry, 2005 , vol. 70, # 6 p. 2200 - 2205

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Citation Number: 29

Abstract

Diastereoselective alkylations of metalated conformationally locked 4-tert- butylcyclohexanecarbonitrile are highly diastereoselective with magnesium and copper counterions but only modestly diastereoselective with lithium as the counterion. Selective generation of diverse metalated nitriles is readily achieved through bromine-magnesium,- copper, and-lithium exchange reactions of the corresponding bromonitrile or, for lithium, ...