A Unified Strategy for the Asymmetric Synthesis of Highly Substituted 1,2-Amino Alcohols Leading to Highly Substituted Bisoxazoline Ligands
Bijay Shrestha, Brennan T. Rose, Casey L. Olen, Aaron Roth, Adon C. Kwong, Yang Wang, Scott E. Denmark
Abstract
A general procedure for the asymmetric synthesis of highly substituted 1,2-amino alcohols in high yield and diastereoselectivity is described that uses organometallic additions of a wide range of nucleophiles to tert-butylsulfinimines as the key step. The addition of organolithium reagents to these imines follows a modified Davis model. The diastereoselectivity for this reaction depends significantly on both the nucleophile and electrophile. These highly substituted 1,2-amino alcohols are used to synthesize stereochemically diverse and structurally novel, polysubstituted 2,2′-methylene(bisoxazoline) ligands in high yields.
Topics & Concepts
ChemistryNucleophileElectrophileYield (engineering)ReagentMethyleneEnantioselective synthesisCombinatorial chemistryOrganic chemistryStereochemistryCatalysisMaterials scienceMetallurgyAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisSynthesis and Catalytic Reactions