Base-promoted diastereoselective α-alkylation of borane N-((S)-1′-phenylethyl)azetidine-2-carboxylic acid ester complexes

2018 ◽  
Vol 16 (32) ◽  
pp. 5833-5845
Author(s):  
Eiji Tayama ◽  
Ryotaro Nishio ◽  
Yoshiaki Kobayashi

Synthesis of optically-active α-substituted azetidine-2-carboxylic acid esters starting from (S)-1-phenylethylamine was successfully demonstrated via diastereoselective N-boration followed by α-alkylation.

2014 ◽  
Vol 10 ◽  
pp. 141-149 ◽  
Author(s):  
Moustafa Sherief Moustafa ◽  
Saleh Mohammed Al-Mousawi ◽  
Maghraby Ali Selim ◽  
Ahmed Mohamed Mosallam ◽  
Mohamed Hilmy Elnagdi

Novel routes for the preparation of 2-amino-4H-pyran-3-carbonitrile 9, amino-arylbenzoic acid ester derivatives 13a,b, 2-aminotetrahydro-4H-chromene-3-carbonitrile 18, 3-amino-4-cyanotetrahydronaphthalene-2-carboxylic acid ester 26 and 4-amino-3,5-dicyanophthalic acid ester derivatives 37a–c were developed. The synthetic methods utilize one-pot reactions of acetylene carboxylic acid esters, α,β-unsaturated nitriles and/or active methylenenitriles in the presence of L-proline or DABCO. Plausible mechanisms are suggested for the formation of the products. Finally, these compounds were used for the efficient synthesis of 6-amino-5-cyanonicotinic acid ester derivatives 31a,b, ethyl 4-amino-5H-pyrano[2,3-d]pyrimidine-6-carboxylates 33a,b, 4-amino-6H-pyrrolo[3,4-g]quinazoline-9-carbonitrile 39, and 1,7-diamino-6-(N'-hydroxycarbamimidoyl)-3-oxo-5-phenyl-3H-isoindole-4-carboxylate (40).


2003 ◽  
Vol 22 (9-10) ◽  
pp. 917-925 ◽  
Author(s):  
S. H. Hilal ◽  
S. W. Karickhoff ◽  
L. A. Carreira ◽  
B. P. Shrestha

2013 ◽  
Vol 125 (5) ◽  
pp. 1145-1149 ◽  
Author(s):  
WEIDONG JIANG ◽  
BIN XU ◽  
ZHEN XIANG ◽  
SHENGTIAN HUANG ◽  
FUAN LIU ◽  
...  

1989 ◽  
Vol 22 (11) ◽  
pp. 4382-4384 ◽  
Author(s):  
Patty Wisian-Neilson ◽  
M. Safiqul Islam ◽  
S. Ganapathiappan ◽  
Devri L. Scott ◽  
Krishan S. Raghuveer ◽  
...  

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