73854-01-0Relevant academic research and scientific papers
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.
Practical implications of boron-to-zinc transmetalation for the catalytic asymmetric arylation of aldehydes
Jimeno, Ciril,Sayalero, Sonia,Fjermestad, Torstein,Colet, Gisela,Maseras, Feliu,Pericas, Miquel A.
, p. 1098 - 1101 (2008/09/20)
(Chemical Equation Presented) Faster than believed: Transmetalation from aryl boronic acids and triaryl boroxines to diethylzinc takes place within minutes following a two-step, low-energy pathway (see picture), according to density functional calculations and reaction microcalorimetry measurements. The experimental conditions for a practical, atom-economical, and highly enantioselective catalytic arylation of a variety of aldehydes have been developed from these data.
