Intramolecular generation and [2,3]-sigmatropic rearrangement of oxonium ylides

1986 ◽  
Vol 108 (19) ◽  
pp. 6060-6062 ◽  
Author(s):  
Michael C. Pirrung ◽  
John A. Werner
Keyword(s):  
Sigmatropic Rearrangement ◽  
Oxonium Ylides

Enantioselective tandem formation and [2,3]-sigmatropic rearrangement of cyclic propargylic oxonium ylides catalyzed by dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate]

2001 ◽  
Vol 41 (4) ◽  
pp. 283-296 ◽  
Author(s):  
Hideyuki Tsutsui ◽  
Maya Matsuura ◽  
Kazuishi Makino ◽  
Seiichi Nakamura ◽  
Makoto Nakajima ◽  
...  
Keyword(s):  
Sigmatropic Rearrangement ◽  
Oxonium Ylides

scholarly journals Copper-Catalyzed Synthesis of Axially Chiral Biaryls with Diaryliodonium Salts as Arylation Reagents

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3223
Author(s):  
Ji-Wei Zhang ◽  
Shao-Hua Xiang ◽  
Shaoyu Li ◽  
Bin Tan
Keyword(s):  
Amino Alcohols ◽  
Sigmatropic Rearrangement ◽  
Synthetic Route ◽  
Mild Conditions ◽  
Good Substrate ◽  
Diaryliodonium Salts ◽  
Axially Chiral

NOBIN and BINAM derivatives harboring biaryl frameworks are recognized as a class of important atropisomers with versatile applications. Here, we present an efficient synthetic route to access such compounds through copper-catalyzed domino arylation of N-arylhydroxylamines or N-arylhydrazines with diaryliodonium salts and [3,3]-sigmatropic rearrangement. This reaction features mild conditions, good substrate compatibility, and excellent efficiency. The practicality of this protocol was further extended by the synthesis of biaryl amino alcohols.

An Umpolung Oxa-[2,3] Sigmatropic Rearrangement Employing Arynes for the Synthesis of Functionalized Enol Ethers

2021 ◽  
Author(s):  
Rahul N. Gaykar ◽  
Malini George ◽  
Avishek Guin ◽  
Subrata Bhattacharjee ◽  
Akkattu T. Biju
Keyword(s):  
Sigmatropic Rearrangement ◽  
Enol Ethers
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