β-Amino Alcohol Organocatalysts for Asymmetric Additions

The Pd-catalysed asymmetric allylic alkylation reactions of sulfamidate imines

“…This synthetic sequence therefore offers efficient access to highly functionalised allylated β-amino alcohols, which can serve as useful synthetic building blocks. 52,53 Scheme 4. Substrate scope with in situ generated 1,3-dipoles.…”

Simple primary β-amino alcohols as organocatalysts for the asymmetric Michael addition of β-keto esters to nitroalkenes

“… 2 However, it is always a challenging task to design and synthesize a new class of multifunctional organocatalysts and to explore them as self-determining and eco-friendly catalysts in asymmetric synthesis. In recent years, we are continuously exploring the multifunctional β-amino alcohol organocatalysts X ( Scheme 1 ), 3 that are easily derived from commercially available amino acids in one or two steps and are less sensitive to air, show low toxicity and are eco-friendly. This amino alcohol X contains an amino group acting as a basic or covalent enamine formation site, a non-covalent hydroxyl group acting as a hydrogen bonding site in a single molecule and also the substituents at α- and β-positions, which might also be effective in controlling the enantioselective reaction course ( Scheme 1 ).…”

N-Alkylation/aldol reaction of α-aldimino thioesters: a facile three-component coupling reaction

“…Various synthetic 1,2-amino alcohol derivatives have also been employed as drugs for therapeutic purposes, chiral auxiliaries, and metal ligands in catalytic asymmetric synthesis. 2 We have reported new approaches to this class of compound via asymmetric reduction of 1,2-imino ketones, 3 diastereoselective addition to chiral imines, 4 titanium tetraiodide-mediated reductive addition reactions, 5 and crossed pinacol-type reductive coupling of aldehydes with imines. 6 In addition to these studies, we have been interested in the Umpolung reactions using α-imino esters 1 and related compounds, and have disclosed several interesting features.…”