Transition metal catalyzed radical cyclization: new preparative route to .gamma.-lactams from allylic alcohols via the [3.3]-sigmatropic rearrangement of allylic trichloroacetimidates and the subsequent ruthenium-catalyzed cyclization of N-allyltrichloroacetamides

1992 ◽  
Vol 57 (6) ◽  
pp. 1682-1689 ◽  
Author(s):  
Hideo Nagashima ◽  
Hidetoshi Wakamatsu ◽  
Nobuyasu Ozaki ◽  
Tsutomu Ishii ◽  
Masakazu Watanabe ◽  
...  
Keyword(s):  
Transition Metal ◽  
Radical Cyclization ◽  
Sigmatropic Rearrangement ◽  
Allylic Alcohols ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Preparative Route

Radical Strategy for the Transition-Metal-Catalyzed Synthesis of γ-Lactones: A Review

Synthesis ◽  
2020 ◽  
Vol 52 (24) ◽  
pp. 3855-3865
Author(s):  
Ren-Jie Song ◽  
Bin Wei ◽  
Ke-Wei Li ◽  
Yan-Chen Wu ◽  
Shi-Qi Tong
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Recent Progress ◽  
Food Additives ◽  
Radical Cyclization ◽  
Biological Molecules ◽  
Cyclization Reactions ◽  
Unsaturated Carboxylic Acids ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

The γ-lactone skeleton is very important component of various natural products, biological molecules, food additives, and perfumes. As a result, much effort has been made towards such compounds. In this review, we summarize recent progress in transition-metal-catalyzed annulation reactions for the formation of γ-lactone derivatives through a radical pathway. Various reagents, such as anhydrides, Togni’s reagent, TMSN3, arenesulfonyl chlorides, arenediazonium salts, dibenzoyl peroxides, O-benzoylhydroxylamine, NFSI, and α-halocarboxylic compounds, used in radical cyclization reactions are described, and the mechanisms of these radical annulation reactions are also discussed.1 Introduction2 Annulations of Alkenes with Anhydrides3 Annulations of Unsaturated Carboxylic Acids with Nucleophiles4 Annulations of Alkenes with α-Halocarboxylic Compounds5 Conclusions and Outlook

Transition-metal-catalyzed radical cyclization: copper-catalyzed cyclization of allyl trichloroacetates to trichlorinated .gamma.-lactones

1990 ◽  
Vol 55 (3) ◽  
pp. 985-990 ◽  
Author(s):  
Hideo Nagashima ◽  
Koji Seki ◽  
Nobuyasu Ozaki ◽  
Hidetoshi Wakamatsu ◽  
Kenji Itoh ◽  
...  
Keyword(s):  
Transition Metal ◽  
Radical Cyclization ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed
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