201852-50-8Relevant academic research and scientific papers
On the use of boronates in the Petasis reaction
Jourdan, Hélène,Gouhier, Géraldine,Van Hijfte, Luc,Angibaud, Patrick,Piettre, Serge R.
, p. 8027 - 8031 (2005)
Alcohols are solvents of choice to react boronates, aldehydes and either primary or secondary amines. Thus, while the reaction proceeds sluggishly, or not at all, in aprotic solvents, the desired aminoacids are in most cases obtained in high yields when c
Water as the reaction medium for multicomponent reactions based on boronic acids
Candeias, Nuno R.,Cal, Pedro M.S.D.,André, Vania,Duarte, M. Teresa,Veiros, Luís F.,Gois, Pedro M.P.
experimental part, p. 2736 - 2745 (2010/05/17)
Water is a suitable medium for the Petasis-borono-Mannich multicomponent reaction. Salicylaldehyde, glyoxalic acid, glycoaldehyde and glyoxal were reacted with several boronic acids and different amines affording alkylaminophenols, 2H-chromenes, α-amino a
Pinacolyl boronic esters as components in the Petasis reaction
Koolmeister, Tobias,S?dergren, Mikael,Scobie, Martin
, p. 5965 - 5968 (2007/10/03)
The multicomponent reaction of boronic esters with imine or iminium species (generated in situ by reaction of amines with glyoxylic acid) has received little attention in the literature despite the current interest in the corresponding reactions of boronic acids (Petasis reaction). Moreover, the use of boronic esters in this reaction is particularly attractive since chiral esters could act as auxiliaries in a novel enantioselective process. We set out to establish whether boronic esters were general substrates in the Petasis reaction. Pinacolyl boronic esters were selected for study as a model substrate for more complex homochiral boronic esters because of their ease of synthesis and chemical stability. We found that pinacolyl boronic esters do not react with imines derived from primary amines and glyoxylic acid under standard conditions. By contrast, imines derived from secondary amines and glyoxylic acid react readily with vinylboronic esters but less readily with heteroaryl- or arylboronic esters.
