Development of polymer-supported chiral aminoalcohols derived from biomass and their application to asymmetric alkylation

Abstract

pp xxx-xxx Development of polymer-supported chiral aminoalcohols derived from biomass and their application to asymmetric alkylation

Levoglucosenone and Its New Applications: Valorization of Cellulose Residues

“…Two alternative synthetic methodologies were explored for the preparation of Wang resin‐bounded 1,2‐amino alcohols, depending if the amine‐based ring opening of the epoxide took place before or after the binding of the chiral residue to the solid support. Evaluation of the inductive capacity of the solid‐supported ligands in the addition of Et 2 Zn to benzaldehyde afforded similar results to those previously noted in solution …”

“…This would allow additional benefits compared to their soluble counterparts, as the ligand could be recovered by simple filtration, hence avoiding chromatographic purifications and simplifying the recycling of the valuable chiral materials . The strategy developed to achieve our goals relied on the synthesis of compound 21 using similar reactions described above (Scheme ) …”

An Efficient and Practical Chemoenzymatic Route to (3R,3aR,6R,6aR)-Hexahydrofuro[3,2-b]furan-6-amino-3-ol (6-Aminoisomannide) from Renewable Sources

“…In particular the manipulation of the chiral pool available from biomass, which appears very attractive for the synthesis of asymmetric auxiliaries 7 and organocatalysts, 8 could represent a simple and economical way to obtain chiral amino-alcohols endowed with interesting stereochemical features. 9 Among the biomass-based precursors suitable for the synthesis of amines and aminoalcohols, a great deal of attention has been addressed to (3R,3aR,6R,6aR)-hexahydrofuro [3,2-b]furan-3,6-diol and its (3R,3aR,6S,6aR) diastereoisomer, also known as isomannide and isosorbide respectively. They are renewable, inexpensive and commercially available chiral compounds derived from the dehydration of sorbitol and mannitol, respectively, which are waste products formed during the processing of corn oil and byproducts from the starch industry.…”