Group-Assisted-Purification Chemistry Strategy for the Efficient Assembly of Cyclic Fused Pyridinones

Synthesis ◽  
2021 ◽  
Author(s):  
Di Ke ◽  
You Wu ◽  
Lei Zhang ◽  
Jiaan Shao ◽  
Yongping Yu ◽  
...  
Keyword(s):  
Amino Acid ◽  
Amino Alcohols ◽  
Aliphatic Amines ◽  
Amino Acid Esters ◽  
Reaction Condition ◽  
Excellent Yield ◽  
Three Component Reaction ◽  
Work Up ◽  
Acid Esters

A group-assisted-purification (GAP) chemistry strategy based Ugi four-center three-component reaction (Ugi-4C-3CR) was explored. The reaction proceeded well to deliver the cyclic fused pyridinones selectively. Moreover, the reaction condition was mild and avoided additional chromatography or recrystallization work-up. Also, wide variations in substrates, such as anilines and aliphatic amines as well as amino alcohols and amino acid esters were all tolerated and achieved in good to excellent yields. Importantly, ladder-type cyclic fused pyridinones can be further constructed with excellent yield of 91%.

scholarly journals Aluminum-mediated one-pot conversion of .ALPHA.-amino acid esters to threo 2-amino alcohols with high diastereoselectivity.

1989 ◽  
Vol 37 (10) ◽  
pp. 2867-2869 ◽  
Author(s):  
Shinzo KANO ◽  
Yoko YUASA ◽  
Tsutomu YOKOMATSU ◽  
Shiroshi SHIBUYA
Keyword(s):  
Amino Acid ◽  
Amino Alcohols ◽  
Amino Acid Esters ◽  
One Pot ◽  
Alpha Amino Acid ◽  
Acid Esters

ChemInform Abstract: Simple Methodology for the Preparation of Amino Alcohols from Amino Acid Esters Using NaBH4-Methanol in THF.

ChemInform ◽  
2011 ◽  
Vol 42 (40) ◽  
pp. no-no
Author(s):  
R. S. B. Goncalves ◽  
A. C. Pinheiro ◽  
E. T. da Silva ◽  
J. C. S. da Costa ◽  
C. R. Kaiser ◽  
...  
Keyword(s):  
Amino Acid ◽  
Amino Alcohols ◽  
Amino Acid Esters ◽  
Acid Esters

Preparation of N-protected α-amino alcohols by acetoxyborohydride reduction of N-protected α-amino acid esters

1990 ◽  
Vol 55 (3) ◽  
pp. 761-765 ◽  
Author(s):  
Milan Souček ◽  
Ján Urban ◽  
David Šaman
Keyword(s):  
Elevated Temperature ◽  
Amino Acid ◽  
Amino Alcohols ◽  
Protecting Groups ◽  
Amino Acid Esters ◽  
Acid Esters

N-Protected α-amino alcohols were prepared by reduction of N-protected α-amino acid esters by sodium acetoxyborohydride in dioxane at elevated temperature. The reductions proceed with excellent yields and without racemisation. Reduction of the carbamate protecting groups was not observed.

Simple Methodology for the Preparation of Amino Alcohols from Amino Acid Esters Using NaBH4–Methanol in THF

2011 ◽  
Vol 41 (9) ◽  
pp. 1276-1281 ◽  
Author(s):  
R. S. B. Gonçalves ◽  
A. C. Pinheiro ◽  
E. T. da Silva ◽  
J. C. S. da Costa ◽  
C. R. Kaiser ◽  
...  
Keyword(s):  
Amino Acid ◽  
Amino Alcohols ◽  
Amino Acid Esters ◽  
Acid Esters
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