109428-73-1

Basic information

• Product Name: 3-((1S,2S,3S,4R)-3-Phenyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one
• Synonyms: 3-((1S,2S,3S,4R)-3-Phenyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one
• CAS NO: 109428-73-1
• Molecular Weight: 283.327
• Mol File: 109428-73-1.mol

Chemical Properties

• CAS DataBase Reference: 3-((1S,2S,3S,4R)-3-Phenyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-((1S,2S,3S,4R)-3-Phenyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one(109428-73-1)
• EPA Substance Registry System: 3-((1S,2S,3S,4R)-3-Phenyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one(109428-73-1)

Safety Data

• Hazardous Substances Data: 109428-73-1(Hazardous Substances Data)

Upstream product

• 109299-93-6 3-((E)-3-phenyl-2-propenoyl)-1,3-oxazolidin-2-one 
• 542-92-7 cyclopenta-1,3-diene 

Relevant articles and documents

Asymmetric Diels-Alder Reactions Catalyzed by Chiral Lanthanide(III) Trifluoromethanesulfonates. Unique Structure of the Triflate and Stereoselective Synthesis of Both Enantiomers Using a Single Chiral Source and a Choice of Achiral Ligands

Chiral lanthanide trifluoromethanesulfonates (triflates) were developed and the unique structure of the triflates was revealed.In the presence of a catalytic amount of the triflate, acyl-1,3-oxazolidin-2-ones reacted with cyclopentadiene to afford the Die

An air stable moisture resistant titanium triflate complex as a lewis acid catalyst for C-C bond forming reactions

An air and moisture stable C3-symmetric titanium(IV) triflate, supported by a tripodal amine-(tris-phenolate) ligand, has been synthesized and characterized by X-ray crystallography and shown to be a good Lewis acid catalyst for a range of aza-Diels-Alder, Diels-Alder, syn aldol, allylation, and alkylation reactions.

Chiral 2,2′-Binaphthyldiimine-Nickel(II) Complexes as Lewis Acid Catalysts for Enantioselective Diels-Alder Reactions

The preparation and application of a novel class of chiral Lewis acid catalysts based on chiral 2,2′-binaphthyldiimine ligands are described. Among the binaphthyldiimine-metal complexes tested, N,N′ -bis(2-quinolylmethylene)-1,1′-binaphthyl-2,2′-diamine-Ni(II) complex was found to be an efficient chiral Lewis acid catalyst for asymmetric Diels-Alder reactions (endo: up to 96% ee) between cyclopentadiene and 3-alkenoyl-2-oxazolidinones. This catalyst is easy to prepare and is efficient; that is, 1 mol% of the Ni(II) catalyst promoted a Diels-Alder reaction between cyclopentadiene and 3-acryloyl-2-oxazolidinone smoothly with high enantioselectivity (endo: 90% ee).

The preparation and utility of bis(sulfinyl)imidoamidine ligands for the copper-catalyzed Diels-Alder reaction

The design and preparation of a novel class of ligands based on the sulfinyl imine functionality is described. In particular, an efficient and modular synthesis of bis(sulfinyl)imidoamidine (siam) ligands is reported. The versatility of the synthetic sequence is demonstrated by the preparation of various analogues to explore the effect of substitution about the ligand framework on catalytic activity. The utility of the siam ligands in asymmetric catalysis is demonstrated in the Cu(II)-catalyzed Diels-Alder reaction where highly enantio- and diastereoselective reactions are reported for a range of N-acyloxazolidinone dienophile and diene substrate combinations. Of particular note is the efficiency of these asymmetric catalysts for reactions involving challenging and relatively unreactive acyclic diene substrates. Finally, structural data are provided for several ligands as well as metal-ligand complexes.

Asymmetric Diels-Alder reactions catalyzed by chiral Ni(II)-binaphthyldiimine complexes

Ni(II)-N,N′-Bis(2-quinolylmethylene)-1,1′-binaphthyl- 2,2′-diamine complex was found to be an efficient chiral Lewis acid catalyst for asymmetric Diels-Alder reactions (endo: up to 94% ee) between cyclopentadiene (1) and 3-alkenoyl-2-oxazolidinones (2). I

Scandium(III) triflate/isopropyl-pybox complex as an efficient catalyst for asymmetric Diels-Alder reaction

The chiral scandium (III) triflate/i-Pr-pybox complex efficiently catalyzes the asymmetric Diels-Alder reaction of 1,3-dienes with acyl-1,3-oxazolidin-2-ones (1a-c) afford the corresponding adducts in good yields with up to 90% ee. The reaction can be car

(Phosphino-oxazoline)copper(II) complexes as chiral catalysts for enantioselective Diels-Alder reactions

(Phosphino-oxazoline)copper(II) complexes with bulky aryl groups at phosphorus were found to be excellent catalysts for Diels-Alder additions of 3-acryloyl-1,3-oxazolidin-2-one. Diels-Alder reactions with a range of substrates were investigated. Enantioselectivities of up to 97% ee were achieved.

A C2-symmetric titanium(IV) complex as a Lewis acid promoter in Diels-Alder reaction

3-Aza-3-benzyl-1,5-dihydroxy-1,5-diphenylpentane 1, a C2-symmetric diol has been prepared by the reaction of benzylamine and styrene oxide using a modified procedure. The corresponding titanium complex has been effectively utilised as a Lewis acid promoter in Diels-Alder reactions. The reactions are performed with cyclopentadiene and various dienophiles under different reaction conditions. The Diels-Alder adducts have been obtained in moderate to good yield and with high endo selectivity.

Asymmetric Diels-Alder reaction catalyzed by a chiral ytterbium trifluoromethanesulfonate

In the presence of a catalytic amount of chiral ytterbium trifluoromethanesulfonate (triflate), acyl-1,3-oxazolidin-2-ones or methacrolein reacted with cyclopentadiene to afford the corresponding Diels-Alder adduct in high yields and with moderate to exce