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

Abstract

Simple primary β-amino alcohols X act as an efficient organocatalysts in the asymmetric Michael addition of β-keto esters A with nitroalkenes B affording highly pure chiral Michael adducts C.

Thiourea fused γ-amino alcohol organocatalysts for asymmetric Mannich reaction of β-keto active methylene compounds with imines

“… 2 In recent years, we have also developed various β-amino alcohols X, which were utilized effectively as organocatalyst in different enantioselective reactions. 3 Most recently, we have also reported the effectiveness of di-amino alcohol organocatalyst Y in aldol reactions. 4 Based on these backgrounds, we have designed a new thiourea fused γ-amino alcohol organocatalyst Z ( Scheme 1 ) that contains thiourea and hydroxy groups acting as hydrogen bonding sites, and a tert -amino group acting as a basic and steric influence site.…”

New boro amino amide organocatalysts for asymmetric cross aldol reaction of ketones with carbonyl compounds

“…5 Our group is also exploring new polyfunctional organocatalysts based on primary amino alcohols and amino amides, which are easily derived from commercially available amino acids, in numerous asymmetric reactions. 6 However, only a few examples have been reported on the polyfunctional organocatalysts with boron functional groups as Lewis acidic sites, such as thiourea-boronic acid X by Takemoto 7 and proline boronate Y by Whiting, 8 so far.…”