199277-77-5

Upstream product

• 1620-75-3 2-Cyano-6-methylpyridine 
• 3182-95-4 L-Phenylalaninol 
• 18368-63-3 6-chloro-2-picoline 
• 75866-71-6 (4S)-4-benzyl-4,5-dihydro-1,3-oxazole 
• 5315-25-3 2-bromo-6-methylpyridine 
• 129821-92-7 methyl 6-methylpicolinimidate 
• 133522-38-0 (S)-2-Amino-1-benzylethanol 
• 1795-98-8 rac-phenylalaninol 

Relevant academic research and scientific papers

Chiral Alkyl Amine Synthesis via Catalytic Enantioselective Hydroalkylation of Enecarbamates

Chiral alkyl amines are omnipresent as bioactive molecules and synthetic intermediates. The catalytic and enantioselective synthesis of alkyl amines from readily accessible precursors is challenging. Here we develop a nickel-catalyzed hydroalkylation method to assemble a wide range of chiral alkyl amines from enecarbamates (N-Cbz-protected enamines) and alkyl halides with high regio- and enantioselectivity. The method works for both nonactivated and activated alkyl halides and is able to produce enantiomerically enriched amines with two minimally differentiated α-alkyl substituents. The mild conditions lead to high functional group tolerance, which is demonstrated in the postproduct functionalization of many natural products and drug molecules, as well as the synthesis of chiral building blocks and key intermediates to bioactive compounds.

Ligand-Controlled Regiodivergent Hydroalkylation of Pyrrolines

Nickel hydride (NiH) catalyzed hydrocarbonation has emerged as an efficient approach to construct new C?C bonds containing at least one C(sp3) center. However, the regioselectivity of this reaction is by far dictated by substrates. Described here is a strategy to achieve two different regioselectivites of hydroalkylation of the same substrates by using ligand control. This strategy enables the first regiodivergent hydroalkylation of 3-pyrrolines, yielding both 2- and 3-alkylated pyrrolidines, valuable synthetic intermediates and common motifs in many bioactive molecules. This method demonstrates broad scope and high functional-group tolerance, and can be applied in late-stage functionalizations.

Palladium-Catalyzed Amide-Directed Enantioselective Hydrocarbofunctionalization of Unactivated Alkenes Using a Chiral Monodentate Oxazoline Ligand

A Pd-catalyzed amide-directed enantioselective hydrocarbofunctionalization of unactivated alkenes with C-H nucleophiles has been developed using a chiral monodentate oxazoline (MOXin) ligand. Various indoles react at C3 position with aminoquinoline-coupled 3-alkenamides to give γ addition products in good to excellent yield and enantioselectivity. This study represents an important advance of the development of chiral monodentate oxazoline ligands, which have been underexplored for asymmetric catalysis.

Secondary Phosphine Oxide Preligands for Palladium-Catalyzed C–H (Hetero)Arylations: Efficient Access to Pybox Ligands

C–H arylations of oxazolines were accomplished with a well-defined palladium catalyst derived from a secondary bisdiamantyl phosphine oxide. The single-component secondary phosphine oxide (SPO)-palladium complex enabled C–H activations with aryl bromides

Palladium-Catalyzed C-2 C-H Heteroarylation of Chiral Oxazolines: Diverse Synthesis of Chiral Oxazoline Ligands

A direct, efficient, and practical protocol to install a chiral oxazoline unit onto aryl/heteroaryl rings via palladium-catalyzed C-H functionalization of 2-positions of oxazolines with a variety of halides using dppe as the ligand has been developed. Var

Chiral oxazolinylpyridines as ligands for enantioselective palladium catalysed allylic substitution

Chiral oxazolinylpyridines were prepared and assessed in the enantioselective palladium catalysed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate. Enantioselectivity up to 91% was obtained.