Catalytic Asymmetric Umpolung Allylation/2-Aza-Cope Rearrangement for the Construction of α-Tetrasubstituted α-Trifluoromethyl Homoallylic Amines

2019 ◽  
Vol 21 (17) ◽  
pp. 6940-6945 ◽  
Author(s):  
Chong Shen ◽  
Ruo-Qing Wang ◽  
Liang Wei ◽  
Zuo-Fei Wang ◽  
Hai-Yan Tao ◽  
...  
Keyword(s):  
Cope Rearrangement ◽  
Homoallylic Amines ◽  
Catalytic Asymmetric

scholarly journals Synthesis of Homoallylic Amines via 2-Aza-Cope Rearrangement

Synfacts ◽  
2006 ◽  
Vol 2006 (10) ◽  
pp. 1061-1061
Author(s):  
S. Kobayashi ◽  
M. Sugiura ◽  
C. Mori
Keyword(s):  
Cope Rearrangement ◽  
Homoallylic Amines

Iridium-Catalyzed Asymmetric Umpolung Allylation of N-Fluor­enyl Imines to Prepare 1,4-Disubstituted Homoallylic Amines

Synlett ◽  
2017 ◽  
Vol 28 (16) ◽  
pp. 2051-2056 ◽  
Author(s):  
Dawen Niu ◽  
Liqiang Wan ◽  
Lan Tian ◽  
Jie Liu
Keyword(s):  
Natural Products ◽  
Cope Rearrangement ◽  
Allylic Substitution ◽  
Reaction Discovery ◽  
Homoallylic Amines ◽  
Synthetic Utility ◽  
Reaction Proceeds ◽  
Conventional Methods

The discovery and development of an Ir-catalyzed asymmetric umpolung allylation of imines is discussed here. This method produces 1,4-disubstituted homoallylic amines, a class of compounds that are difficult to access by conventional methods. This reaction proceeds through a sequence involving an allylation and a 2-aza-Cope rearrangement event. The unique mechanistic feature of this reaction could be the reason for its broad substrate scope. The products of this reaction are useful intermediates for various bioactive and natural products. Besides its immediate synthetic utility, we expect this transformation to inspire the development of other umpolung functionalizations of imines and Ir-catalyzed asymmetric allylic substitution (AAS) reactions.1 Introduction2 Reaction Discovery3 Substrate Scope4 Conclusion

Recent advances in catalytic asymmetric aza-Cope rearrangement

2021 ◽  
Vol 57 (81) ◽  
pp. 10469-10483
Author(s):  
Liang Wei ◽  
Chun-Jiang Wang
Keyword(s):  
System Design ◽  
Catalytic System ◽  
Recent Progress ◽  
Cope Rearrangement ◽  
Recent Advances ◽  
Design Mechanism ◽  
Catalytic Asymmetric

This review highlights the recent progress in catalytic asymmetric aza-Cope rearrangement, and covers important features of these studies including catalytic system design, mechanism insight, stereochemistry analysis and synthetic applications.

Sequential Ir‐Catalyzed Allylation/ 2‐aza‐Cope Rearrangement Strategy for the Construction of Chiral Homoallylic Amines †

2020 ◽  
Vol 38 (8) ◽  
pp. 807-811 ◽  
Author(s):  
Ruo‐Qing Wang ◽  
Chong Shen ◽  
Xiang Cheng ◽  
Zuo‐Fei Wang ◽  
Hai‐Yan Tao ◽  
...  
Keyword(s):  
Cope Rearrangement ◽  
Homoallylic Amines
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