Radical cyclization reactions of .alpha.-silyl amine .alpha.,.beta.-unsaturated ketone and ester systems promoted by single electron transfer photosensitization

1991 ◽  
Vol 113 (23) ◽  
pp. 8847-8863 ◽  
Author(s):  
Yoon T. Jeon ◽  
Chao Pin Lee ◽  
Patrick S. Mariano
Keyword(s):  
Electron Transfer ◽  
Radical Cyclization ◽  
Single Electron ◽  
Unsaturated Ketone ◽  
Single Electron Transfer ◽  
Cyclization Reactions ◽  
Alpha Beta

Single-Electron-Transfer Strategy for Reductive Radical Cyclization: Fe(CO)5 and Phenanthroline System

2016 ◽  
Vol 18 (19) ◽  
pp. 4900-4903 ◽  
Author(s):  
Joon Young Hwang ◽  
Jong Hwa Baek ◽  
Tae Il Shin ◽  
Jung Ha Shin ◽  
Jae Won Oh ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Radical Cyclization ◽  
Single Electron ◽  
Single Electron Transfer

N-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides

2016 ◽  
Vol 52 (70) ◽  
pp. 10621-10624 ◽  
Author(s):  
Arvind K. Yadav ◽  
Lal Dhar S. Yadav
Keyword(s):  
Electron Transfer ◽  
Room Temperature ◽  
Radical Cyclization ◽  
Regioselective Synthesis ◽  
Single Electron ◽  
Single Electron Transfer

A highly regioselective synthesis of 3-iminodihydroindoles using N-methylanilines and isocyanides at room temperature is described. The protocol utilizes N-hydroxyphthalimide as a new single electron transfer photoredox catalyst.

scholarly journals α,γ-Dioxygenated amides via tandem Brook rearrangement/radical oxygenation reactions and their application to syntheses of γ-lactams

2021 ◽  
Vol 17 ◽  
pp. 688-704
Author(s):  
Mikhail K Klychnikov ◽  
Radek Pohl ◽  
Ivana Císařová ◽  
Ullrich Jahn
Keyword(s):  
Electron Transfer ◽  
Radical Cyclization ◽  
Biologically Active ◽  
Single Electron Transfer ◽  
Wide Scope ◽  
Carbonyl Groups ◽  
Cyclization Reactions ◽  
Chiral Epoxides ◽  
Brook Rearrangement ◽  
High Yields

Pyrrolidones are common heterocyclic fragments in various biologically active compounds. Here, a two-step radical-based approach to γ-lactams bearing three to four stereocenters starting from epoxides, N-allylic silylacetamides and TEMPO is reported. The sequence starts with a new tandem nucleophilic substitution/Brook rearrangement/single electron transfer-induced radical oxygenation furnishing orthogonally protected α,γ-dioxygenated N-allylamides with wide scope, mostly good yields, and partly good diastereo- and enantioselectivity for defined combinations of chiral epoxides and chiral amides. This represents a very rare example of an oxidative geminal C–C/C–O difunctionalization next to carbonyl groups. The resulting dioxygenated allylic amides are subsequently subjected to persistent radical effect-based 5-exo-trig radical cyclization reactions providing functionalized pyrrolidones in high yields as diastereomeric mixtures. They converge to 3,4-trans-γ-lactams by base-mediated equilibration, which can be easily further diversified. Stereochemical models for both reaction types were developed.

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