33870-37-0

Upstream product

• 100-65-2 N-Phenylhydroxylamine 
• 814-68-6 acryloyl chloride 
• 98-95-3 nitrobenzene 
• 586-96-9 Nitrosobenzene 
• 107-02-8 acrolein 

Downstream Products

• 439598-79-5 N-isopropoxy-N-phenylacrylamide 
• 439598-81-9 N-tert-butoxy-N-phenylacrylamide 
• 111533-12-1 tris(N-phenylacryloylhydroxylaminato)chromium(III) 
• 105877-39-2 tris(N-phenylacryloylhydroxylaminato)indium 
• 111315-13-0 bis(N-phenylacryloylhydroxylaminato)iron(II) 
• 115451-55-3 bis(N-phenylacrylhydroxamato)tin(II) 

Relevant academic research and scientific papers

N-HETEROCYCLIC CARBENE (NHC) CATALYZED SYNTHESIS OF HYDROXAMIC ACIDS

A process for preparing hydroxamic acids is provided. The process comprises reacting an aldehyde with a nitroso compound in the presence of a N-heterocyclic carbene (NHC) catalyst.

N-heterocyclic carbene (NHC)-catalyzed direct amidation of aldehydes with nitroso compounds

(Chemical Equation Presented) NHC-catalyzed direct amidation of aldehydes with nitroso compounds is a powerful method for the synthesis of N-arylhydroxamic acids. A variety of aryl, alkyl, alkenyl, and heterocyclic aldehydes were found to give excellent yields of the corresponding N-arylhydroxamic acids. This chemistry was also extended to the synthesis of chiral N-arylhydroxamic acids by kinetic resolution of α-branched aldehydes, a domino amidation-redox amination reaction of acrolein, and a three-component reaction for the synthesis of N-arylaziridines.

Enantioselective Diels-Alder reactions with N-hydroxy-N-phenylacrylamide

Matrix presented The use of hydroxamic acids as templates for Lewis acid catalyzed enantioselective Diels-Alder reactions has been examined. A very simple chiral Lewis acid, prepared by mixing optically pure binaphthol with 3 equiv of trimethylaluminum, catalyzes the [4 + 2] cycloaddition of N-hydroxy-N-phenylacrylamide with cyclopentadiene at 0°C in high yield (>96%) and with a fairly good level of enantioselectivity (91% ee). Facile conversion of the products to the corresponding alcohols or aldehydes makes the hydroxamic acid intermediates particularly useful.

N-alkoxyacrylamides as substrates for enantioselective Diels-Alder reactions

Matrix presented The use of N-alkoxyacrylamides as substrates for Lewis acid catalyzed Diels-Alder reactions has been examined. Enantioselectivities up to 92% ee have been achieved using very simple chiral Lewis acids prepared from triisobutylaluminum and 2,2-dimethyl-α,α,α′,α′-tetra-1-naphthalenyl- TADDOL (1-NaphtTADDOL). The use of Yamamoto's Zn-BINOL, easily prepared from Et2Zn and 1,1′-bi-2-naphthol (BINOL), proved to be even more efficient, and enantioselectivities up to 96% ee were achieved.