Issue 19, 2011

Asymmetric additive-free aryl addition to aldehydes using perhydrobenzoxazines as ligands and boroxins as aryl source

Abstract

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.

Graphical abstract: Asymmetric additive-free aryl addition to aldehydes using perhydrobenzoxazines as ligands and boroxins as aryl source

Supplementary files

Article information

Article type
Paper
Submitted
06 May 2011
Accepted
21 Jun 2011
First published
21 Jun 2011

Org. Biomol. Chem., 2011,9, 6691-6699

Asymmetric additive-free aryl addition to aldehydes using perhydrobenzoxazines as ligands and boroxins as aryl source

R. Infante, J. Nieto and C. Andrés, Org. Biomol. Chem., 2011, 9, 6691 DOI: 10.1039/C1OB05717K

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