Base-Catalyzed Bifunctional Addition to Amides and Imides at Low Temperature. A New Pathway for Carbonyl Hydrogenation

被引：72

作者：

John, Jeremy M. ^{[1
]}

Takebayashi, Satoshi ^{[1
]}

Dabral, Nupur ^{[1
]}

Miskolzie, Mark ^{[1
]}

Bergens, Steven H. ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 23期

关键词：

HYDROXYCYCLOPENTADIENYL RUTHENIUM HYDRIDE; ASYMMETRIC HYDROGENATION; ENANTIOSELECTIVE HYDROGENATION; AROMATIC KETONES; PROTON-TRANSFER; COMPLEXES; MECHANISM; REDUCTION; IMINES; ALCOHOLS;

D O I：

10.1021/ja401294q

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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-M-2[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-d(8). Details of the origins of the enantioselection for the desymmetrization of meso-cyclic imides by hydrogenation with 8-K are also described herein.

引用

页码：8578 / 8584

页数：7

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