14185-43-4

Upstream product

• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 541-41-3 chloroformic acid ethyl ester 
• 28570-76-5 (E)-ethanone-1-phenyl-O-(phenylmethyl)oxime 
• 10341-75-0 (E)-1-phenylethanone oxime 

Downstream Products

• 29882-69-7 potassium syn-(R)-1-phenylethanediazoate 
• 163562-74-1 (+)-(R)-N-methyl-N-propargyl-1-phenylethylamine 
• 5933-40-4 (R)-(+)-N,α-dimethylbenzylamine 
• 143678-71-1 (+)-(R)-ethyl N-nitroso-N-(1-phenylethyl)carbamate 
• 33290-10-7 (R)-ONN-1-Phenylazoxyethan 

Relevant academic research and scientific papers

Synthesis of limonene β-amino alcohol from (R)-(+)-α-methylbenzylamine and (+)-limonene 1,2-epoxide

Two new compounds of β-amino alcohol are obtained using (R) - (+) - α-methylbenzylamine as starting material which is converted into two amines. Each of these compounds reacted in excess with a 1: 1 mixture of cis and trans-limonene oxide in the presence of water as a catalyst. The products obtained show that β-amino alcohol derived from trans-limonene oxide is obtained and unreacted cis-limonene oxide from the reaction mixture as well as the amine is attained. Whereas the addition of the synthesized carbamate of the same primary amine over the 1: 1 mixture of cis and trans -limonene oxide in the presence of water results in the hydrolysis product and the recovery of unreacted trans-limonene oxide.

Cyanative self-condensation of aromatic aldehydes promoted by VO(O iPr)3-Lewis base as a cooperative catalyst

Self-condensation of aromatic aldehydes with trimethylsilyl cyanide proceeded by the cooperative catalytic effect of VO(OiPr)3 and a Lewis base to give the corresponding O-acylated cyanohydrins. The reaction conversion and selectivity were strongly dependent on the solvent used, the Lewis base, and the presence of oxygen. All the nine kinds of aromatic aldehydes considered herein afforded the O-acylated cyanohydrins with excellent selectivity under an O2 atmosphere.

Asymmetric synthesis of primary amines via the spiroborate-catalyzed borane reduction of oxime ethers

The enantioselective borane reduction of O-benzyloxime ethers to primary amines was studied under catalytic conditions using the spiroborate esters 5-10 derived from nonracemic 1,2-amino alcohols and ethylene glycol. Effective catalytic conditions were achieved using only 10% of catalyst 5 derived from diphenylvalinol in dioxane at 0°C resulting in complete conversion to the corresponding primary amine in up to 99% ee.

Diastereoselective carbozincation of propargylic amines

The carbometalation of propargylic amines derived from methylbenzylamine takes place with good 1,3-diastereoselection in the presence of Lewis acids.