A Three-Component Enantioselective Cyclization Reaction Catalyzed by an Unnatural Amino Acid Derivative

被引：23

作者：

de Gracia Retamosa, Maria ^{[1
,2
,3
]}

Ruiz-Olalla, Andrea ^{[1
,2
,3
]}

Bello, Tamara ^{[1
,2
,3
]}

de Cozar, Abel ^{[1
,2
,3
,4
]}

Cossio, Fernando P. ^{[1
,2
,3
]}

机构：

[1] Univ Basque Country UPV EHU, Dept Quim Organ 1, P Manuel Lardizabal 3, Donostia San Sebastian 20018, Spain

[2] Univ Basque Country UPV EHU, Ctr Innovac Quim Avanzada ORFEO CINQA, P Manuel Lardizabal 3, Donostia San Sebastian 20018, Spain

[3] DIPC, P Manuel Lardizabal 3, Donostia San Sebastian 20018, Spain

[4] Ikerbasque, Basque Fdn Sci, Bilbao 48011, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 03期

关键词：

asymmetric catalysis; heterocycles; multicomponent reactions; organocatalysis; synthetic methods; ASYMMETRIC MICHAEL ADDITION; ALDOL REACTIONS; AMARYLLIDACEAE ALKALOIDS; PROLINE ESTERS; ORGANOCATALYSIS; EFFICIENT; KETONES; (-)-PANCRACINE; NITROOLEFINS; NITROALKENES;

D O I：

10.1002/anie.201708952

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new diastereo- and enantioselective three-component cyclization reaction is described. The reaction takes place between a ketone, a carboxylic acid, and a nitroalkene to yield a bicyclic octahydro-2H-indol-2-one scaffold possessing three chiral centers. This reaction involves a rearrangement of the nitro group under simple thermal conditions. A plausible mechanism is proposed for this new reaction based on DFT calculations and isotope-labeling experiments. A new concise enantioselective synthesis of the alkaloid (+)-pancracine is presented as an example of the potential of this novel organocatalytic cyclization reaction in the synthesis of natural products.

引用

页码：668 / 672

页数：5

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