A novel method to obtain racemic 1-nitroalkan-2-ols by reaction of bromonitromethane with a variety of aldehydes and promoted by SmI2 is reported. On the basis of these results, the chiral version has also been performed with chiral N,N-dibenzyl amino aldehydes, affording the corresponding enantiopure 3-amino-1-nitroalkan-2-ols with good stereoselectivity.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/jo061465w | DOI Listing |
Soft Matter
May 2020
Centro de Ciências Naturais e Humanas, Universidade Federal do ABC, 09210-580, Santo André, Brazil.
The self-assembly of model [P]RWG lipopeptides (P: l-proline, R: l-arginine, W: l-tryptophan, G: l-glycine), containing one or two aliphatic octadecyl (C) chains in water and cyclohexanone/water solutions was examined. The self-assembly of mixtures of these RWG and PRWG lipopeptides was also investigated. These materials presented a similar critical aggregation concentration of ∼4.
View Article and Find Full Text PDFOrg Lett
September 2018
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering , Lanzhou University, Lanzhou 730000 , P. R. China.
A dearomative remote activation strategy for the asymmetric functionalization of benzylic C-H bonds of heteroaryl aldehydes under bifunctional Brønsted base catalysis has been developed. The in situ generated o-QDMs-type dienolate intermediates were efficiently and stereoselectively trapped by nitroolefins through an asymmetric Michael/nitro-aldol cascade reaction. Using this strategy, a wide variety of synthetically significant tetrahydrodibenzothiophene and tetrahydrodibenzofuran derivatives were synthesized in good yields with high enantioselectivities.
View Article and Find Full Text PDFInorg Chem
July 2013
Department of Chemical Sciences, Tezpur University, Napaam, Assam, India 784028.
Two chiral Schiff-base complexes of copper(II) have been successfully encapsulated inside the cavity of zeolite-NaY via a "ship in a bottle" synthesis method. The presence of the two complexes inside the cages of zeolite-Y has been confirmed based on various spectrochemical and physicochemical techniques, viz. FTIR, UV-vis/DRS, ESR, XPS, CV, EDX, SEM, and TGA.
View Article and Find Full Text PDFJ Org Chem
February 2008
Department of Applied Chemistry, Faculty of Engineering, Kanagawa University, Yokohama, 221-8686, Japan.
A stereoselective and efficient total synthesis of optically active tetrodotoxin (TTX) is described. A polyfunctionalized key cyclitol compound containing branched-chains for the synthesis of TTX was prepared from D-glucose employing the Henry reaction (Nitro aldol reaction) as the key transformation. Stereoselective construction of the alpha-azido-aldehyde branched-chain was achieved via the key spiro alpha-chloroepoxide intermediate.
View Article and Find Full Text PDFJ Org Chem
September 2006
Departamento de Química Organica e Inorganica, Facultad de Química, Universidad de Oviedo, Julian Clavería 8, 33071 Oviedo, Spain.
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!