Cooperative N-Heterocyclic Carbene/Palladium-Catalyzed Enantioselective Umpolung Annulations

被引：302

作者：

Guo, Chang ^{[1
]}

Fleige, Mirco ^{[1
]}

Janssen-Mueller, Daniel ^{[1
]}

Daniliuc, Constantin G. ^{[1
]}

Glorius, Frank ^{[1
]}

机构：

[1] Univ Munster, Organisch Chem Inst, Corrensstr 40, D-48149 Munster, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 25期

关键词：

TRANSITION-METAL CATALYSIS; ASYMMETRIC-SYNTHESIS; PHOTOREDOX CATALYSIS; GAMMA-BUTYROLACTONES; ALLYLIC ALKYLATIONS; CARBENE CATALYSIS; RELAY CATALYSIS; DUAL CATALYSIS; NHC CATALYSIS; ALDEHYDES;

D O I：

10.1021/jacs.6b04364

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A combination of NHC organocatalysis and transition-metal catalysis gives rise to fundamentally new cooperative reactivity and enables the regio- and enantioselective annulation reaction between enals and vinyl benzoxazinanones. The cooperative umpolung annulation eliminates mutual deactivation and leads to a diverse set of benzazepine derivatives in good yields with excellent enantioselectivities (up to 99% ee). The development of such a cooperative catalytic system dramatically expands the scope of NHC organocatalysis by opening up new metal-catalyzed reaction pathways for homoenolate intermediates.

引用

页码：7840 / 7843

页数：4

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