109299-92-5

Usage

Chemical Properties

off-white to light yellow crystalline powder

Synthesis Reference(s)

Synthetic Communications, 26, p. 261, 1996 DOI: 10.1080/00397919608003613

InChI:InChI=1/C7H9NO3/c1-2-3-6(9)8-4-5-11-7(8)10/h2-3H,4-5H2,1H3/b3-2+

Upstream product

• 497-25-6 dimethylenecyclourethane 
• 623-68-7 crotonic anhydride 
• 623-68-7 trans-crotonic anhydride 
• 60420-28-2 3-butyryloxazolidin-2-one 
• 765310-91-6 (E)-2-butenoic pivalic anhydride 
• 107-93-7 (E)-but-2-enoic acid 
• 625-35-4 trans-chrotonyl chloride 

Downstream Products

• 200408-59-9 (R,R)-3-[3-(2',5'-dihydro-5'-oxo-2'-furyl)]butanoyl-1,3-oxazolidin-2-one 
• 173937-02-5 2-benzyl-5-methyl-4-(2'-oxo-1',3'-oxazolidine-3'-carbonyl)-3-phenylisoxazolidine 

Relevant academic research and scientific papers

Total synthesis of (+)-suaveolindole: Establishment of its absolute configuration

This communication describes two approaches toward the total synthesis of (+)-suaveolindole. The initial strategy uses a 6-exo-Heck cyclization to generate a transient sp3 carbopalladate. This intermediate was successfully coupled with an indole 3-stannane to assemble the majority of the carbon framework of the natural product. However, due to problems described herein, this interesting route was not viable. To reach our target, lessons learned from the first strategy directed us to develop a significant extension of the Ireland ester enolate rearrangement in which the tetra-substituted isopropylidene group and the α-disposed carboxymethyl function are introduced in a single event. This key reaction enables a remarkably concise inaugural synthesis of (+)-suaveolindole. Copyright

Direct coupling procedure for the synthesis of N-acyl-2-oxazolidinones derived from α,β-unsaturated carboxylic acids

An efficient direct coupling procedure for the synthesis of N-acyl-2-oxazolidinones derived from α,β-unsaturated carboxylic acids is described in which 2-chloro-1-methylpyridinium iodide is employed as the dehydrating agent.

One-pot dehydrogenation of carboxylic acid derivatives to α,β-unsaturated carbonyl compounds under mild conditions

Carboxylic acid derivatives such as N-acyl-2-oxazolidones, δ-lactones, and δ-lactams were smoothly dehydrogenated to the corresponding α,β-unsaturated carbonyl compounds in one-pot manner at -78°C just by treating their lithium enolates with N-tert- butyl

Visible light photocatalytic asymmetric synthesis of pyrrolo[1,2-: A] indoles via intermolecular [3+2] cycloaddition

The intermolecular diastereoselective and enantioselective synthesis of pyrrolo[1,2-a]indoles is developed through a [3+2] cycloaddition between silyl-indole derivatives and α,β-unsaturated N-acyl oxazolidinones by merging photocatalysis and Lewis acid catalysis.

Asymmetric FeII-Catalyzed Thia-Michael Addition Reaction to α,β-Unsaturated Oxazolidin-2-one Derivatives

A highly enantioselective FeII-catalyzed thia-Michael addition to α,β-unsaturated carbonyl derivatives was developed. The scope of the reaction was demonstrated with a selection of aromatic, heterocyclic and aliphatic thiols, and various Michael acceptors. The corresponding β-thioethers were obtained in good to excellent yields (up to 98%) and moderate to excellent enantioselectivities (up to 96:4 er). Unusual hepta-coordination of the metal and chelation to α,β-unsaturated oxazolidin-2-one derivatives allowed the construction of a coherent model rationalizing the enantioselective event. DFT calculations support the proposed model for observed stereoselectivities.

Hantzsch Ester as a Photosensitizer for the Visible-Light-Induced Debromination of Vicinal Dibromo Compounds

The debromination of vicinal dibromo compounds to generate alkenes usually requires harsh reaction conditions and the addition of catalysts. Just recently the visible-light-induced debromination of vicinal dibromo compounds emerged as a possible alternative to commonly used methods, but the substrate scope of this reaction is limited and a photocatalyst is necessary for the successful conversion of the starting compounds. A catalyst-free visible-light-induced debromination of vicinal dibromo compounds with a base-activated Hantzsch ester as photosensitizer is reported. The method has a wide substrate scope and a broad functional-group compatibility.

A protocol for accessing the β-azidation of α,β-unsaturated carboxylic acids

This contribution reports the preparation and use of a new immobilized catalyst, PS-DABCOF (9), which has been specifically designed to access for the first time the efficient β-azidation of α,β-unsaturated carboxylic acids.

Intermolecular mono-and dihydroamination of activated alkenes using a recoverable gold catalyst

A combination of gold chloride organometallic complex and a silver salt was used to catalyze intermolecular hydroamination of activated alkenes, i.e aza-Michael reactions. The gold-catalyzed reactions of activated alkenes with nitrogen substrates were investigated and found to afford various mono-and dihydroamination products, the latter being rare and original. After flash chromatography, gold NHC catalyst could be recovered as a gold hydroxide NHC complex. When combined with a silver salt, the gold complex lead again to an active hydroamination catalyst.

Synthetic study of diversifolin: The construction of 11-oxabicyclo[6.2.1] undec-3-ene core using ring-closing metathesis

Stereoselective synthesis of a potential intermediate bearing 11-oxabicyclo[6.2.1]undec-3-ene core, a common scaffold of biologically active germacrane-type sesquiterpenes, has been achieved. Synthetic features involve formal 1,3-asymmetric induction, unu

Enantioselective conjugate addition of hydrazines to α,β- unsaturated imides. Synthesis of chiral pyrazolidinones

This manuscript describes a highly enantioselective conjugate hydrazine addition to α,β-unsaturated imides. The achiral template used has a significant impact on product enantioselectivity. Reactions at lower temperatures provide a protocol to add substit