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Base-catalyzed bifunctional addition to amides and imides at low temperature. A new pathway for carbonyl
Jeremy M John1, Satoshi Takebayashi, Nupur Dabral
1Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2.
Abstract:
Mono- or dideprotonation at the N-H groups of the Noyori ketone hydrogenation catalyst trans-[RuH2((R)-BINAP)((R,R)-dpen)] (1a) yields trans-M[RuH2((R,R)-HNCH(Ph)CH(Ph)NH2)((R)-BINAP)], where M = K(+)(8-K) or Li(+) (8-Li), or trans-M2[RuH2((R,R)-HNCH(Ph)CH(Ph)NH)((R)-BINAP)], where M = Li(+) (8-M'2), which have unprecedented activity toward the hydrogenation of amide and imide carbonyls at low temperatures in THF-d8. Details of the origins of the enantioselection for the desymmetrization of meso-cyclic imides by hydrogenation with 8-K are also described herein.
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