Organocatalytic, enantioselective, intramolecular oxa-Michael reaction of alkoxyboronate: a new strategy for enantioenriched 1-substituted 1,3-dihydroisobenzofurans.

Autor: Raveendra B; Department of Chemistry, Indian Institute of Science Education and Research Bhopal , Bhauri, Bhopal 462066, India., Das BG, Ghorai P
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2014 Nov 07; Vol. 16 (21), pp. 5580-3. Date of Electronic Publication: 2014 Oct 22.
DOI: 10.1021/ol502614n
Abstrakt: An unprecedented strategy for the synthesis of enantioenriched 1-substituted 1,3-dihydroisobenzofurans via an enantioselective oxa-Michael reaction of o-alkoxyboronate containing chalcone (II) has been accomplished employing cinchona alkaloid based squaramide bifunctional organocatalyst in the presence of proton source. The corresponding alkoxyboronate intermediates have been readily prepared in situ from o-formyl chalcones using neutral borane as hydride source and a tertiary amine moiety which is a counterpart of the catalyst.
Databáze: MEDLINE