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

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

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

Carbopalladation-depalladation of homoallylic amines and sulfides

1977 ◽  
Vol 142 (1) ◽  
pp. C15-C18 ◽  
Author(s):  
Robert A. Holton ◽  
Richard A. Kjonaas
Keyword(s):  
Homoallylic Amines

scholarly journals Stereoselective Tandem Iridium-Catalyzed Alkene Isomerization-Cope Rearrangement of ω-diene Epoxides: Efficient Access to Acyclic 1,6-Dicarbonyl Compounds

2021 ◽  
Author(s):  
Rahul Suresh ◽  
Itai Massad ◽  
Ilan Marek
Keyword(s):  
Bond Cleavage ◽  
Cope Rearrangement ◽  
Dicarbonyl Compounds ◽  
Alkene Isomerization ◽  
Efficient Access

The Cope rearrangement of 2,3-divinyloxiranes, a rare example of epoxide C-C bond cleavage, results in 4,5-dihydrooxepines which are amenable to hydrolysis, furnishing 1,6-dicarbonyl compounds containing two contiguous stereocenters at the 3- and 4- positions. We employ...

Cope rearrangement of 9-methylenebarbaralane. Complete line shape analysis

1973 ◽  
Vol 38 (6) ◽  
pp. 1210-1215 ◽  
Author(s):  
Linda G. Greifenstein ◽  
Joseph B. Lambert ◽  
Michael J. Broadhurst ◽  
Leo A. Paquette
Keyword(s):  
Shape Analysis ◽  
Line Shape ◽  
Cope Rearrangement ◽  
Line Shape Analysis

A Versatile Hexadiene Synthesis by Decarboxylative sp3—sp3 Coupling/Cope Rearrangement.

ChemInform ◽  
2006 ◽  
Vol 37 (48) ◽  
Author(s):  
Shelli R. Waetzig ◽  
Dinesh K. Rayabarapu ◽  
Jimmie D. Weaver ◽  
Jon A. Tunge
Keyword(s):  
Cope Rearrangement
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