133146-85-7

Usage

InChI:InChI=1/C6H11NO3/c1-5(8)4-6(9)7(2)10-3/h4H2,1-3H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 1117-97-1 N,0-dimethylhydroxylamine 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 78191-00-1 N-Methoxy-N-methylacetamide 
• 75-36-5 acetyl chloride 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 674-82-8 4-methyleneoxetan-2-one 

Downstream Products

• 1621269-84-8 (2R,3R)-2-acetyl-N-methoxy-N-methyl-4-nitro-3-phenylbutanamide 
• 1621269-83-7 (2S,3R)-2-acetyl-N-methoxy-N-methyl-4-nitro-3-phenylbutanamide 
• 1643654-76-5 (2S,3S)-2-acetyl-N-methoxy-N-methyl-4-nitro-3-phenylbutanamide 
• 1643654-77-6 (2S,3S)-2-acetyl-N-methoxy-3-(4-methoxyphenyl)-N-methyl-4-nitrobutanamide 
• 1643654-78-7 (2S,3S)-2-acetyl-N-methoxy-N-methyl-4-nitro-3-(4-nitrophenyl)butanamide 
• 1643654-79-8 (2S,3S)-2-acetyl-3-(2-bromophenyl)-N-methoxy-N-methyl-4-nitrobutanamide 
• 1643654-82-3 (2S,3R)-2-acetyl-N-methoxy-N-methyl-3-(nitromethyl)-5-phenylpentanamide 
• 1643654-98-1 (2S,3S)-2-((R)-1-hydroxyethyl)-N-methoxy-N-methyl-4-nitro-3-phenylbutanamide 
• 1643654-95-8 (2S,3S)-2-((S)-1-hydroxyethyl)-N-methoxy-N-methyl-4-nitro-3-phenylbutanamide 
• 191731-37-0 N-methoxy-N-methyl-2-(phenylthio)acetamide 

Relevant academic research and scientific papers

Enantioselective Cyclopropanation with α-Alkyl-α-diazoesters Catalyzed by Chiral Oxazaborolidinium Ion: Total Synthesis of (+)-Hamavellone B

Chiral oxazaborolidinium ion-catalyzed asymmetric cyclopropanation of α- or α,β-substituted acroleins with α-alkyl-α-diazoesters has been developed. With this methodology, chiral functionalized cyclopropanes containing a quaternary stereogenic center were obtained with high to excellent enantioselectivities (up to >99% ee). The synthetic utility of optically enriched functionalized cyclopropane was demonstrated in the first total synthesis of (+)-hamavellone B, which establishes the absolute configuration of natural (+)-hamavellone B.

Copper-catalyzed oxyvinylation of diazo compounds

A copper(I)-catalyzed vinylation of diazo compounds with vinylbenziodoxolone reagents (VBX) as partners is reported. The transformation tolerates diverse functionalities on both reagents delivering polyfunctionalized vinylated products. The strategy was successfully extended to a three-component/intermolecular version with alcohols. The obtained products contain synthetically versatile functional groups, such as an aryl iodide, an ester, and an allylic leaving group, enabling further modification.

Photochemical Alkene Isomerization for the Synthesis of Polysubstituted Furans and Pyrroles under Neutral Conditions

A photochemical approach to polysubstituted heterocycles using UV-induced alkene isomerization is described. The method allows for the synthesis of disubstituted furans and pyrroles under mild and neutral conditions and also provides access to a class of trisubstituted furans pertinent to natural-product synthesis. The method has broad functional-group tolerance and many richly decorated heterocycles have been prepared incorporating functional groups that are unstable under Br?nsted and Lewis acidic conditions.

Intermolecular acetoxyaminoalkylation of α-diazo amides with (diacetoxyiodo)benzene and amines

Multicomponent reactions of diazo compounds have attracted much attention in recent years. Such transformations are generally conducted by applying transition metal catalysis and involve the corresponding metal carbenes as key intermediates. In this letter, a metal-free three-component intermolecular acetoxyaminoalkylation of α-diazo amides with tertiary aryl amines and (diacetoxyiodo)benzene is presented.

Synthesis of Enantiomerically Pure β-Hydroxy Ketones via β-Keto Weinreb Amides by a Condensation/Asymmetric-Hydrogenation/Acylation Sequence

An established route to enantiomerically pure β-hydroxy ketones proceeds through the asymmetric hydrogenation of β-keto esters, an ester/amide exchange, and the use of the resulting β-hydroxy amide for the acylation of an organometallic compound. We shortened this route by showing that β-keto Weinreb amides are hydrogenated with up to 99 % ee in the presence of [Me2NH2]+{[RuCl(S)-BINAP]2(μ-Cl)3}–(0.5 mol-%) at room temp./5 bar. These Weinreb amides were prepared by seemingly obvious yet unprecedented condensations of lithiated N-methoxy-N-methylacetamide with carboxylic chlorides (51–87 % yield). The resulting β-hydroxy Weinreb amides were used for the acylation of organolithium and Grignard reagents. They thus gave enantiomerically pure β-hydroxy ketones (28 examples). A selection of these compounds gave anti-1,3-diols after another C=O bond hydrogenation, or syn-1,3-diols by a Narasaka–Prasad reduction.

Enantioselective Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds

Enantioselective catalytic methods allowing the addition of both a nucleophile and an electrophile onto diazo compounds give a fast access into important building blocks. Herein, we report the highly enantioselective oxyalkynylation of diazo compounds usi

α-Crotyl-α-difluoroboranyloxy-amides: Structure and Reactivity of Isolable Intermediates in Stereospecific α-Ketol Rearrangements

The stereospecific BF3-mediated α-ketol rearrangement of β-hydroxy-α-ketoamides yields isolable 2-difluoroboranyloxy-3-keto-amides. X-ray and NMR analysis reveal a carbonyl coordination of the boron by the amide not the ketone. The boron complexes are air-stable solids, can be purified by silica gel chromatography, and exhibit novel reactivity in bromination and superior stereoselectivity in dipolar cycloaddition reactions.

Organocatalytic enantio- and diastereoselective conjugate addition to nitroolefins: When ketoamides surpass ketoesters

Our findings on the bifunctional squaramide-catalyzed enantioselective conjugate addition of ketoamides to nitroolefins are disclosed. It appears that simple acyclic methylene ketoamides, unlike the extensively studied ketoesters, afford the products in excellent diastereoselectivities, and maintain high yields and enantioselectivities. Moreover, competition and kinetic studies were conducted to rationalize the observed reactivity and selectivity. The high level of diastereocontrol, along with the amenability of the amide group to postfunctionalization, dramatically increase the synthetic usefulness of the transformation.

Regio- and diastereoselective crotylboration of vic-tricarbonyl compounds

Crotylboration of vic-diketoamides and vic-diketo esters was achieved with high diastereoselectivity and complementary regioselectivity. Whereas (E)-crotylboration of α,β-diketoamides resulted in high yields (91-99 %) of β-crotylated products obtained as a single diastereomer (anti), Lewis acid promoted crotylboration of α,β-diketo esters yielded the α-crotylated species with the anti product as main diastereomer. (E)-Crotylboration of α,β-diketoamides resulted in high yields (91-99 %) of β-crotylated products obtained as a single diastereomer (anti). Lewis acid promoted crotylboration of α,β-diketo esters yielded the α-crotylated species with the anti product as main diastereomer. Copyright

Ru-catalyzed asymmetric hydrogenation of 3-oxoglutaric acid derivatives via solvent-assisted pinpoint recognition of carbonyls in close chemical propinquity

Upon comparison of hydrogenation rates of various β-ketocarboxylic acid derivatives, β-ketoamides were found to be hydrogenated slightly faster than β-ketoesters in EtOH in the presence of [RuCl(benzene)(S)- SunPhos]Cl at 70 °C with 20 bar of hydrogen. In THF these differences were so sharpened that β-ketoamides were hydrogenated even faster than in EtOH while the esters were extremely slow. Based on these findings, a series of 3-oxoglutaric acid derived with ester and amide moieties on the two ends were hydrogenated to 3-hydroxyl products with high enantioselectivities.