Enantio- and Diastereoselective Nucleophilic Addition of N-tert-Butylhydrazones to Isoquinolinium Ions through Anion-Binding Catalysis

被引：36

作者：

Matador, Esteban ^{[3
,4
]}

Iglesias-Siguenza, Javier ^{[3
,4
]}

Monge, David ^{[3
,4
]}

Merino, Pedro ^{[5
]}

Fernandez, Rosario ^{[3
,4
]}

Lassaletta, Jose M. ^{[1
,2
]}

机构：

[1] US, CSIC, Inst Invest Quim, C Amer Vespucio 49, Seville 41092, Spain

[2] CINQA, ORFEO, Ctr Innovac Quim Avanzada, C Amer Vespucio 49, Seville 41092, Spain

[3] Univ Seville, Dept Quim Organ, C Prof Garcia Gonzalez 1, Seville 41012, Spain

[4] CINQA, ORFEO, Ctr Innovac Quim Avanzada, C Prof Garcia Gonzalez 1, Seville 41012, Spain

[5] Univ Zaragoza, CSIC, Inst Biocomputac & Fis Sistemas Complejos BIFI, Zaragoza 50009, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 10期

关键词：

acylation; asymmetric catalysis; dearomatization; hydrazones; organocatalysis; ENANTIOSELECTIVE ADDITION; ASYMMETRIC ADDITION; BUTYL HYDRAZONE; DEAROMATIZATION; ACID; ACTIVATION; N; N-DIALKYLHYDRAZONES; ORGANOCATALYSTS; MECHANISM; PYRIDINES;

D O I：

10.1002/anie.202012861

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly enantio- and diastereoselective thiourea-catalyzed dearomatization of isoquinolines employing N-tert-butylhydrazones as neutral alpha-azo carbanions and masked acyl anion equivalents has been developed. Experimental and computational data supports the generation of highly ordered complexes wherein the chloride behaves as a template for the catalyst, the hydrazone reagent, and the isoquinolinium cation, providing excellent stereocontrol in the formation of two contiguous stereogenic centers. The ensuing selective and high-yielding transformations provide appealing dihydroisoquinoline derivatives.

引用

页码：5096 / 5101

页数：6

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