n-Butyllithium-Induced Tandem [3,3]-Sigmatropic Rearrangement and Carbonyl Olefination of Allyl-1,1-dichlorovinyl Ethers

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.

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

Organic Letters ◽

10.1021/acs.orglett.1c00911 ◽

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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Base-promoted aromatic [3,3] sigmatropic rearrangement of N-acyl-O-arylhydroxylamine derivatives

Tetrahedron ◽

10.1016/j.tet.2018.12.058 ◽

2019 ◽

Vol 75 (5) ◽

pp. 665-673 ◽

Cited By ~ 1

Author(s):

Eiji Tayama ◽

Kazuki Hirano

Keyword(s):

Sigmatropic Rearrangement

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Imino‐λ 3 ‐iodane and Catalytic Amount of I 2 ‐Mediated Synthesis of N ‐Allylsulfenamides via [2,3]‐Sigmatropic Rearrangement

European Journal of Organic Chemistry ◽

10.1002/ejoc.202000961 ◽

2020 ◽

Vol 2020 (41) ◽

pp. 6433-6439

Author(s):

Cody L. Makitalo ◽

Akira Yoshimura ◽

Gregory T. Rohde ◽

Irina A. Mironova ◽

Rosa Y. Yusubova ◽

...

Keyword(s):

Catalytic Amount ◽

Sigmatropic Rearrangement

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Catalyst-Free [2,3]-Sigmatropic Rearrangement Reactions of Photochemically Generated Ammonium Ylides

Synthesis ◽

10.1055/s-0037-1610732 ◽

2019 ◽

Vol 51 (23) ◽

pp. 4348-4358 ◽

Cited By ~ 1

Author(s):

Fang Li ◽

Feifei He ◽

Rene M. Koenigs

Keyword(s):

Visible Light ◽

Sigmatropic Rearrangement ◽

Tertiary Amines ◽

Amino Esters ◽

Catalyst Free ◽

Rearrangement Reaction ◽

Rearrangement Reactions ◽

Free Ammonium

The rearrangement reaction of ammonium ylides furnishes valuable α,α-disubstituted amino esters. In this work, we describe the visible-light photolysis reaction of aryldiazoacetates in the presence of tertiary amines that react via a free ammonium ylide in a sigmatropic rearrangement reaction to provide amino esters in moderate to very good yields (33 examples, up to 97% yield).

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