299160-76-2

Upstream product

• 28541-01-7 (Z)-isopropyl 3-phenylacrylate 
• 60512-85-8 (E)-isopropyl cinnamate 
• 79-15-2 N-bromoacetamide 
• 35077-11-3 α-chloro-N-bromoacetamide 
• 52259-82-2 α,α-dichloro-N-bromoacetamide 
• 127-65-1 chloroamine-T 

Relevant academic research and scientific papers

Chiral-Substituted Poly-N-vinylpyrrolidinones and Bimetallic Nanoclusters in Catalytic Asymmetric Oxidation Reactions

A new class of poly-N-vinylpyrrolidinones containing an asymmetric center at C5 of the pyrrolidinone ring were synthesized from l-amino acids. The polymers, particularly 17, were used to stabilize nanoclusters such as Pd/Au for the catalytic asymmetric oxidations of 1,3- and 1,2-cycloalkanediols and alkenes, and Cu/Au was used for C-H oxidation of cycloalkanes. It was found that the bulkier the C5 substituent in the pyrrolidinone ring, the greater the optical yields produced. Both oxidative kinetic resolution of (±)-1,3- and 1,2-trans-cycloalkanediols and desymmetrization of meso cis-diols took place with 0.15 mol % Pd/Au (3:1)-17 under oxygen atmosphere in water to give excellent chemical and optical yields of (S)-hydroxy ketones. Various alkenes were oxidized with 0.5 mol % Pd/Au (3:1)-17 under 30 psi of oxygen in water to give the dihydroxylated products in >93% ee. Oxidation of (R)-limonene at 25 °C occurred at the C-1,2-cyclic alkene function yielding (1S,2R,4R)-dihydroxylimonene 49 in 92% yield. Importantly, cycloalkanes were oxidized with 1 mol % Cu/Au (3:1)-17 and 30% H2O2 in acetonitrile to afford chiral ketones in very good to excellent chemical and optical yields. Alkene function was not oxidized under the reaction conditions. Mechanisms were proposed for the oxidation reactions, and observed stereo- and regio-chemistry were summarized.

Mechanistic investigation of asymmetric aminohydroxylation of alkenes

Transfer of nitrogen and oxygen in asymmetric aminohydroxylation (AA) has been examined. Electronic as well as steric effect on the nature of oxidizing agent and nitrogen source affect chemo, regio and stereoselectivity in AA reaction. A three cycle mechanistic pathway has been proposed. Results have been rationalized through an addition of alkene to Os=N bond in a [2+2] cycloaddition manner.

Concentration dependence of the sharpless asymmetric amidohydroxylation of isopropyl cinnamate

(Equation presented) A need to prepare large quantities of phenylisoserine for the semisynthesis of paclitaxel prompted us to examine the Sharpless amidohydroxylation reaction to see if it could be run at concentrations greater than those reported in the literature. During these investigations, we discovered that the amount of amidoalcohol produced in the reaction decreased while the diol side product increased as the concentration increased. We discovered that acetamide suppresses this side reaction and allows us to run the chemistry at 0.1 g/mL rather than the 0.014 g/mL reported in the literature.