Nitroethane

Torssell, Kurt; Gothelf, Kurt V.

doi:10.1002/047084289x.rn037

Cited by 2 publications

(2 citation statements)

References 80 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The Henry (nitro aldol) reaction, and its aza analogue, are fundamental C−C bond-forming reactions in organic chemistry. Compared with the development of catalytic enantioselective aldol reactions, there are astonishingly few examples on asymmetric catalytic nitro aldol reactions.…”

mentioning

confidence: 99%

The First Catalytic Asymmetric Aza-Henry Reaction of Nitronates with Imines: A Novel Approach to Optically Active β-Nitro-α-Amino Acid- and α,β-Diamino Acid Derivatives

et al. 2001

Self Cite

View full text Add to dashboard Cite

The Henry (nitro aldol) reaction, 1 and its aza analogue, 2 are fundamental C-C bond-forming reactions in organic chemistry. Compared with the development of catalytic enantioselective aldol reactions, there are astonishingly few examples on asymmetric catalytic nitro aldol reactions. Only the chiral heterobimetallic catalysts reported by Shibasaki et al. have proven to be effective for asymmetric Henry reactions. 3 In extension of this work, they have developed a catalytic asymmetric aza-Henry reaction (nitro-Mannich reaction). 3c When nitromethane was used as the substrate, high enantioselectivities were obtained for this reaction using N-phosphinoylimines. However, 60 mol % of the chiral ligand in the chiral ytterbium catalyst was required, and successful reactions were reported for only nitromethane.This communication presents the first catalytic highly diastereoand enantioselective aza-Henry reaction that proceeds in the absence of a base and with lower catalyst loading. In this reaction, the presence of a base is avoided by the application of silyl nitronates 1a-d instead of nitro compounds for the reaction with R-imino esters 2a-c in the presence of a chiral Lewis acid. It should be noted that a racemic fluoride-induced reaction of silyl nitronates with aldehydes has been described by Seebach et al., 4 and very recently another racemic version of this reaction using Sc(OTf) 3 was reported. 5

show abstract

mentioning

confidence: 99%

The First Catalytic Asymmetric Aza-Henry Reaction of Nitronates with Imines: A Novel Approach to Optically Active β-Nitro-α-Amino Acid- and α,β-Diamino Acid Derivatives

et al. 2001

Self Cite

View full text Add to dashboard Cite

show abstract

“…It is a highly flammable liquid at room temperature and reacts with alkali, strong acids, oxidizers, and metallic oxides. 1 NM is completely miscible with most organic solvents. If not properly handled, stored, or used, it can be dangerous and can detonate.…”

Section: Introductionmentioning

confidence: 99%