Tetrahedron letters

Reductive deoxygenation by Cp 2 ZrHCl: Selective formation of imines via zirconation/hydrozirconation of amides

DJA Schedler, AG Godfrey, B Ganem

Index: Schedler, David J.A.; Godfrey, Alexander G.; Ganem, Bruce Tetrahedron Letters, 1993 , vol. 34, # 32 p. 5035 - 5038

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Citation Number: 50

Abstract

Representative Procedure for the Reduction of Amides by Method A: To a suspension of KH (1 equiv; 25 mg in 1 mL THF, 0°C) was added a solution of 7 (153 mg in 2 mL THF) and after 10 min, the clear anion solution was transferred via syringe to a suspension of Cp 2 ZrHCl (2.4 equiv; 368 mg in 0.5 mL THF, −20°C). After warming gradually to rt (2 h) the reaction was poured into ice-cold hexanes (10 mL) and filtered through Celite using more hexanes (10 mL). ...