127684-94-0

Upstream product

• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 

Downstream Products

• 1027261-89-7 [1-(3,4-dimethoxy-phenyl)-2-methyl-propyl]-carbamic acid tert-butyl ester 
• 234089-61-3 (-)-(1S,2S)-N-benzyl-1,2-bis(3,4-dimethoxyphenyl)-3-methylbutylamine 
• 234089-55-5 (+)-(S)-1,2-bis(3,4-dimethoxyphenyl)-3-methyl-1-butanone 

Relevant academic research and scientific papers

Enantioselective Hydrogenation of Tetrasubstituted α,β-Unsaturated Carboxylic Acids Enabled by Cobalt(II) Catalysis: Scope and Mechanistic Insights

Chiral carboxylic acids are important compounds because of their prevalence in pharmaceuticals, natural products and agrochemicals. Asymmetric hydrogenation of α,β-unsaturated carboxylic acids has been widely recognized as one of the most efficient synthetic approaches to afford such compounds. Although related asymmetric hydrogenation of di- and trisubstituted unsaturated acids with noble metals is well established, asymmetric hydrogenation of challenging tetrasubstituted α,β-unsaturated carboxylic acids is rarely reported. We demonstrate enantioselective hydrogenation of cyclic and acyclic tetrasubstituted α,β-unsaturated carboxylic acids via cobalt(II) catalysis. This protocol showed broad substrate scope and gave chiral carboxylic acids in good yields with excellent enantiocontrol (up to 98 % yield and 99 % ee). Combined experimental and computational mechanistic studies support a CoII catalytic cycle involving migratory insertion and σ-bond metathesis processes. DFT calculations reveal that enantioselectivity may originate from the steric effect between the phenyl groups of the ligand and the substrate.

A new general method for the asymmetric synthesis of 4-alkyl-3-aryl- 1,2,3,4-tetrahydroisoquinolines

A highly enantioselective method for the synthesis of 4-alkyl substituted 1,2,3,4-tetrahydroisoquinolines is reported. The key step relies on the asymmetric synthesis of α-alkylarylacetic acids by alkylation of their corresponding amides employing (S,S)-(+)-pseudoephedrine as chiral inductor. Subsequent Friedel-Crafts acylation, stereocontrolled reductive amination and Pictet-Spengler cyclization affords the title compounds in excellent yields and enantioselectivities.