Spiroborate catalyzed reductions with N, N-diethylaniline borane

BM Coleridge, TP Angert, LR Marks, PN Hamilton…

Index: Coleridge, Brian M.; Angert, Thomas P.; Marks, Lucas R.; Hamilton, Patrick N.; Sutton, Christopher P.; Matos, Karl; Burkhardt, Elizabeth R. Tetrahedron Letters, 2010 , vol. 51, # 46 p. 5973 - 5976

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Citation Number: 5

Abstract

Reduction of esters, amides, and ketones by N, N-diethylaniline borane is accelerated by catalysts derived from spiroborate complexes. Esters are reduced at ambient temperature in less than 4h with this amine borane and 5mol% spiroborate 6. Functional group selectivity shows ketone and tertiary amide reduction is faster than ester or nitrile reduction.