162300-69-8Relevant articles and documents
Asymmetric Catalysis Using Aromatic Aldehydes as Chiral α-Alkoxyalkyl Anions
Yabushita, Kenya,Yuasa, Akihiro,Nagao, Kazunori,Ohmiya, Hirohisa
supporting information, p. 113 - 117 (2019/01/08)
We have developed a new umpolung strategy for catalytically forming a chiral α-alkoxyalkyl anion from an aromatic aldehyde for use in asymmetric synthesis. The reaction between aromatic aldehydes and aryl or allyl electrophiles with a silylboronate utilizing a chiral copper-N-heterocyclic carbene catalyst and a palladium-bisphosphine catalyst in a synergistic manner occurred with high enantioselectivities to deliver the three-component coupling products, chiral silyl-protected secondary alcohol derivatives. Our method features the catalytic generation of enantioenriched chiral α-alkoxyalkylcopper(I) intermediates from aldehydes and their subsequent palladium-catalyzed stereospecific cross-coupling.
Asymmetric additive-free aryl addition to aldehydes using perhydrobenzoxazines as ligands and boroxins as aryl source
Infante, Rebeca,Nieto, Javier,Andres, Celia
experimental part, p. 6691 - 6699 (2011/11/04)
A highly efficient enantioselective aryl addition to aldehydes using boroxins as aryl source and conformationally restricted perhydro-1,3- benzoxazines as ligands is reported. Both enantiomeric forms of chiral arylphenylmethanols and 1,1′-disubstituted diarylmethanols are afforded with excellent yields and enantioselectivities using the same ligand by means of an appropriate combination of boroxin and aromatic aldehyde. The enantiocontrol is not significantly influenced by electronic effects or steric hindrance, even with substituted boroxins. Very homogeneous ee's are reached when substituted arylboroxins are employed, without the use of any class of additive or pre-treatment.
Enantioselective arylations catalyzed by carbohydrate-based chiral amino alcohols
Wouters, Ana Dioneia,Trossini, Gustavo H. G.,Stefani, Helio A.,Luedtke, Diogo S.
experimental part, p. 2351 - 2356 (2010/07/04)
The application of carbohydrate-derived amino alcohols in the asymmetric arylation of aldehydes by using arylboronic acids as the source of transferable aryl groups is described. The best ligand is derived from the readily available sugar D-xylose and it mediates the addition of a range of arylboronic acids to various aromatic aldehydes in excellent yields and high enantiomeric excesses.