scholarly journals Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles

2009 ◽  
Vol 5 ◽  
Author(s):  
Dingqiao Yang ◽  
Ping Hu ◽  
Yuhua Long ◽  
Yujuan Wu ◽  
Heping Zeng ◽  
...  
Keyword(s):  
Secondary Amine ◽  
Ring Opening ◽  
Secondary Amines ◽  
X Ray ◽  
X Ray Crystallography ◽  
Ring Opening Reactions ◽  
Oxabicyclic Alkenes ◽  
First Time ◽  
Asymmetric Ring Opening

Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with various aliphatic and aromatic secondary amines are reported for the first time. The reaction gave the corresponding trans-1,2-dihydronaphthalenol derivatives in good yields with moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl]2 and 5 mol % bisphosphine ligand (S)-p-Tol-BINAP. The trans-configuration of 3f was confirmed by X-ray crystallography.

Chiral P-Containing Palladacycle-Catalyzed Asymmetric Ring-Opening Reactions of Oxabicyclic Alkenes with Alkenyl Boronic Acids

Synlett ◽  
2011 ◽  
Vol 2011 (07) ◽  
pp. 943-946 ◽  
Author(s):  
Xue-Long Hou ◽  
Xiao-Jun Huang ◽  
Dong-Liang Mo ◽  
Chang-Hua Ding
Keyword(s):  
Ring Opening ◽  
Boronic Acids ◽  
Ring Opening Reactions ◽  
Oxabicyclic Alkenes ◽  
Asymmetric Ring Opening

Asymmetric ring-opening reactions of azabenzonorbornadienes through transfer hydrogenation using secondary amines as hydrogen sources: tuning of absolute configuration by acids

2018 ◽  
Vol 5 (21) ◽  
pp. 3077-3082 ◽  
Author(s):  
Dongdong Pu ◽  
Yongyun Zhou ◽  
Fan Yang ◽  
Guoli Shen ◽  
Yang Gao ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Ring Opening ◽  
Transfer Hydrogenation ◽  
Secondary Amines ◽  
Ring Opening Reactions ◽  
Asymmetric Ring Opening

Switching of absolute configuration by acids during palladium and silver co-catalyzed transfer hydrogenation of heterobicycles by secondary amines.

scholarly journals Acid-catalyzed ring-opening reactions of a cyclopropanated 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with alcohols

2017 ◽  
Vol 13 ◽  
pp. 2888-2894 ◽  
Author(s):  
Katrina Tait ◽  
Alysia Horvath ◽  
Nicolas Blanchard ◽  
William Tam
Keyword(s):  
Ring Opening ◽  
Tertiary Alcohol ◽  
Acid Catalysts ◽  
X Ray ◽  
X Ray Crystallography ◽  
Ring Opening Reaction ◽  
Ring Opening Reactions ◽  
Acid Catalyzed

The acid-catalyzed ring-opening reactions of a cyclopropanated 3-aza-2-oxabicylic alkene using alcohol nucleophiles were investigated. Although this acid-catalyzed ring-opening reaction did not cleave the cyclopropane unit as planned, this represent the first examples of ring-openings of cyclopropanated 3-aza-2-oxabicyclo[2.2.1]alkenes that lead to the cleavage of the C–O bond instead of the N–O bond. Different acid catalysts were tested and it was found that pyridinium toluenesulfonate in methanol gave the best yields in the ring-opening reactions. The scope of the reaction was successfully expanded to include primary, secondary, and tertiary alcohol nucleophiles. Through X-ray crystallography, the stereochemistry of the product was determined which confirmed an SN2-like mechanism to form the ring-opened product.

Iridium-Catalyzed Asymmetric Ring-Opening Reactions ofN-Boc-azabenzonorbornadiene with Secondary Amine Nucleophiles

2008 ◽  
Vol 10 (21) ◽  
pp. 4723-4726 ◽  
Author(s):  
Dingqiao Yang ◽  
Yuhua Long ◽  
Huan Wang ◽  
Zhenming Zhang
Keyword(s):  
Secondary Amine ◽  
Ring Opening ◽  
Ring Opening Reactions ◽  
Asymmetric Ring Opening
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