110952-69-7

Upstream product

• 1679-47-6 3-methyltetrahydro-2-furanone 
• 606494-51-3 4-(benzyloxy)-2-methylbutanoic acid 
• 1426307-29-0 C₁₆H₂₄O₃ 
• 1426307-23-4 C₉H₁₈O₃ 
• 1426307-27-8 C₁₆H₂₅NO₂ 
• 116492-51-4 (R)-2-Methyl-4-oxo-butyric acid tert-butyl ester 
• 1426307-12-1 C₉H₁₈O₃ 
• 328241-56-1 N-benzyl-N-(but-3-en-1-yl)formamide 
• 17150-62-8 N-benzyl-3-butenylamine 

Downstream Products

• 69498-26-6 (S)-1-benzyl-3-methylpyrrolidine 

Relevant academic research and scientific papers

Carbonylative C-C bond activation of aminocyclopropanes using a temporary directing group strategy

Temporary directing groups (TDGs) underpin a range of C-C bond activation methodologies; however, the use of TDGs for the regiocontrolled activation of cyclopropane C-C bonds is underdeveloped. In this report, we show how an unusual ring contraction process can be harnessed for TDG-based carbonylative C-C bond activations of cyclopropanes. The method involves the transient installation of an isocyanate-derived TDG, rather than relying on carbonyl condensation events as used in previous TDG-enabled C-C bond activations.

Facile synthesis of versatile enantioenriched α-substituted hydroxy esters through a Bronsted acid catalyzed kinetic resolution

An efficient synthesis of enantioenriched α-substituted γ-hydroxy esters via a kinetic resolution event is described. Bulky racemic esters in the presence of a chiral Bronsted acid selectively lactonize to yield a recoverable enantioenriched hydroxy ester and lactone. These esters are highly versatile building blocks that can readily be converted to synthetically useful materials.

Diaminophosphine oxide ligand enabled asymmetric nickel-catalyzed hydrocarbamoylations of alkenes

Chiral trivalent phosphorus species are the dominant class of ligands and the key controlling element in asymmetric homogeneous transition-metal catalysis. Here, novel chiral diaminophosphine oxide ligands are described. The arising catalyst system with nickel(0) and trimethylaluminum efficiently activates formamide C-H bonds under mild conditions providing pyrrolidones via intramolecular hydrocarbamoylation in a highly enantioselective manner with as little as 0.25% mol catalyst loading. Mechanistically, the secondary phosphine oxides behave as bridging ligands for the nickel center and the Lewis acidic organoaluminum center to give a heterobimetallic catalyst with superior reactivity.

Kinetic resolution in the oxidation of iminium ion to lactam catalysed by aldehyde oxidase.

A rabbit liver enzyme preparation oxidised racemic iminium ions 1 and 2 to optically active lactams 3 and 4 with enantiomer ratios ER/S = 5.5 and 0.14, respectively.