Palladium-catalyzed formal insertion of carbenoids into N,O-aminals: direct access to α-alkoxy-β-amino acid esters

2019 ◽  
Vol 55 (27) ◽  
pp. 3947-3950 ◽  
Author(s):  
Wenhui Wang ◽  
Hanmin Huang
Keyword(s):  
Amino Acid ◽  
Direct Access ◽  
Amino Acid Esters ◽  
Palladium Catalyzed ◽  
Acid Esters

A new and efficient reaction has been developed to synthesize α-alkoxy-β-amino acid esters via palladium-catalyzed formal insertion of carbenoids into N,O-aminals.

Palladium-Catalyzed Intramolecular α-Arylation of α-Amino Acid Esters

2002 ◽  
Vol 67 (2) ◽  
pp. 465-475 ◽  
Author(s):  
Oliver Gaertzen ◽  
Stephen L. Buchwald
Keyword(s):  
Amino Acid ◽  
Amino Acid Esters ◽  
Palladium Catalyzed ◽  
Acid Esters

scholarly journals Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols

2012 ◽  
Vol 8 ◽  
pp. 2004-2018 ◽  
Author(s):  
Rajendra Surasani ◽  
Dipak Kalita ◽  
A V Dhanunjaya Rao ◽  
K B Chandrasekhar
Keyword(s):  
Amino Acid ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Amino Acid Esters ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Acid Esters

Simple and efficient procedures for palladium-catalyzed cross-coupling reactions of N-substituted 4-bromo-7-azaindole (1H-pyrrole[2,3-b]pyridine), with amides, amines, amino acid esters and phenols through C–N and C–O bond formation have been developed. The C–N cross-coupling reaction of amides, amines and amino acid esters takes place rapidly by using the combination of Xantphos, Cs2CO3, dioxane and palladium catalyst precursors Pd(OAc)2/Pd2(dba)3. The combination of Pd(OAc)2, Xantphos, K2CO3 and dioxane was found to be crucial for the C–O cross-coupling reaction. This is the first report on coupling of amides, amino acid esters and phenols with N-protected 4-bromo-7-azaindole derivatives.

Direct Access to N-Unprotected α- and/or β-Tetrasubstituted Amino Acid Esters via Direct Catalytic Mannich-Type Reactions Using N-Unprotected Trifluoromethyl Ketimines

2017 ◽  
Vol 23 (67) ◽  
pp. 17022-17028 ◽  
Author(s):  
Masanao Sawa ◽  
Kazuhiro Morisaki ◽  
Yuta Kondo ◽  
Hiroyuki Morimoto ◽  
Takashi Ohshima
Keyword(s):  
Amino Acid ◽  
Direct Access ◽  
Amino Acid Esters ◽  
Acid Esters

Access to α-Amino Acid Esters through Palladium-Catalyzed Oxidative Amination of Vinyl Ethers with Hydrogen Peroxide as the Oxidant and Oxygen Source

2017 ◽  
Vol 129 (50) ◽  
pp. 16142-16146 ◽  
Author(s):  
Lu Ouyang ◽  
Jianxiao Li ◽  
Jia Zheng ◽  
Jiuzhong Huang ◽  
Chaorong Qi ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
Amino Acid ◽  
Amino Acid Esters ◽  
Vinyl Ethers ◽  
Oxidative Amination ◽  
Palladium Catalyzed ◽  
Acid Esters
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