Enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction.

Autor: Ramachandran PV; Hebert C. Brown Centre for Borane Research, Purdue University, 560 Oval Drive, West Lafayette, IN 47907-2084, USA. chandran@purdue.edu, Chanda PB
Jazyk: angličtina
Zdroj: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2013 Apr 18; Vol. 49 (30), pp. 3152-4. Date of Electronic Publication: 2013 Mar 11.
DOI: 10.1039/c3cc40860d
Abstrakt: A reagent-controlled, diastereo- and enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates has been achieved by the proper choice of solvent, temperature, alkoxy group, and amine for the diisopinocampheylboron-mediated asymmetric enolization-aldolization of phenylacetates. The pure diastereomers can be readily separated by column chromatography.
Databáze: MEDLINE