Autocatalytic one pot orchestration for the synthesis of α-arylated, α-amino esters

2014 ◽  
Vol 50 (20) ◽  
pp. 2632-2634 ◽  
Author(s):  
Stéphane P. Roche ◽  
Shyam S. Samanta ◽  
Marine M. J. Gosselin
Keyword(s):  
One Pot ◽  
Amino Esters ◽  
Autocatalytic System

α-Arylated, α-amino esters are synthesized in one pot, using an AcOH/AcCl autocatalytic system, which promotes simultaneous dehydration–activation before Friedel–Crafts functionalization.

ChemInform Abstract: One-Pot Synthesis of Enantiomerically Pure N-Protected Allylic Amines from N-Protected α-Amino Esters.

ChemInform ◽  
2016 ◽  
Vol 47 (36) ◽  
Author(s):  
Gaston Silveira-Dorta ◽  
Sergio J Alvarez-Mendez ◽  
Victor S Martin ◽  
Jose M Padron
Keyword(s):  
Allylic Amines ◽  
One Pot ◽  
Enantiomerically Pure ◽  
Amino Esters ◽  
One Pot Synthesis

scholarly journals One-Pot Preparation of Chiral β-Amino Esters by Rhodium-Catalyzed Three-Components Coupling Reaction

2002 ◽  
Vol 50 (2) ◽  
pp. 307-308 ◽  
Author(s):  
Toshio Honda ◽  
Hitoshi Wakabayashi ◽  
Kazuo Kanai
Keyword(s):  
Coupling Reaction ◽  
One Pot ◽  
Amino Esters ◽  
Three Components

A Facile One-Pot Synthesis of Chiral β-Amino Esters

Synlett ◽  
2005 ◽  
pp. 2682-2684 ◽  
Author(s):  
Tanasri Bunlaksananusorn ◽  
Florian Rampf
Keyword(s):  
One Pot ◽  
Amino Esters ◽  
One Pot Synthesis

ChemInform Abstract: Autocatalytic One Pot Orchestration for the Synthesis of α-Arylated, α-Amino Esters.

ChemInform ◽  
2014 ◽  
Vol 45 (23) ◽  
pp. no-no
Author(s):  
Stephane P. Roche ◽  
Shyam S. Samanta ◽  
Marine M. J. Gosselin
Keyword(s):  
One Pot ◽  
Amino Esters

scholarly journals One-pot synthesis of enantiomerically pure N-protected allylic amines from N-protected α-amino esters

2016 ◽  
Vol 12 ◽  
pp. 957-962 ◽  
Author(s):  
Gastón Silveira-Dorta ◽  
Sergio J Álvarez-Méndez ◽  
Víctor S Martín ◽  
José M Padrón
Keyword(s):  
Amino Acids ◽  
Allylic Amines ◽  
One Pot ◽  
Enantiomerically Pure ◽  
Amino Esters ◽  
One Pot Synthesis ◽  
Sequential Reduction ◽  
Natural Amino Acids ◽  
Hydroxy Groups

An improved protocol for the synthesis of enantiomerically pure allylic amines is reported. N-Protected α-amino esters derived from natural amino acids were submitted to a one-pot tandem reduction–olefination process. The sequential reduction with DIBAL-H at −78 °C and subsequent in situ addition of organophosphorus reagents yielded the corresponding allylic amines without the need to isolate the intermediate aldehyde. This circumvents the problem of instability of the aldehydes. The method tolerates well both Wittig and Horner–Wadsworth–Emmons organophosphorus reagents. A better Z-(dia)stereoselectivity was observed when compared to the previous one-pot method. The (dia)stereoselectivity of the process was affected neither by the reaction solvent nor by the amount of DIBAL-H employed. The method is compatible with the presence of free hydroxy groups as shown with serine and threonine derivatives.

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