90719-46-3

Upstream product

• 100-51-6 benzyl alcohol 
• 78507-12-7 endo-3-methylbicyclo[2.2.1]hept-5-ene-2-carbonyl chloride 
• 542-92-7 cyclopenta-1,3-diene 
• 15082-42-5 lithium benzyloxide 
• 623-68-7 trans-crotonic anhydride 
• 155227-26-2 C₂₀H₂₇NO₃ 
• 90719-38-3 (4S)-4-benzyl-3-(3-methylbicyclo[2.2.1]hept-5-ene-2-carbonyl)oxazolidin-2-one 
• 90719-37-2 (4S,1'R,2'R,3'S,4'S)-3-[(3'-methylbicyclo[2.2.1]hept-5'-ene-2'-yl)carbonyl]-4-iso-propyloxazolidin-2-one 
• 159849-36-2 (1S,2R,6S,7R,exo)-N-((3'R,4'S,5'S,6'R)-5'-methylbicyclo<2.2.1>heptene-4'-carbonyl)-3-oxa-5-aza-7,10,10-trimethyltricyclo<5.2.1.0^2,6>decan-4-one 

Relevant academic research and scientific papers

Transesterification of N-acyloxazolidinones with alcohol by lanthanum(III) iodide

Transesterification of N-acyloxazolidinones by treatment with an alcohol and lanthanum(III) iodide gives the corresponding esters in good to excellent yields under mild conditions with negligible racemization.

Diels-alder reaction on solid supports using polymer-bound oxazolidinones

Hydroxymethyl resin-bound oxazolidone crotonates undergo Diels-Alder reactions with yields and stereoselectivities comparable to those observed in solution. The stability of the resin to the Lewis acid (Et2AlCl) employed is critical to the success of these cycloadditions.

Asymmetric diels-alder reaction of 2-(p-tolylsulfinyl)-1-indolyl α,β-unsaturated enones

The asymmetric Diels-Alder reaction of chiral 1-[2-(p-tolylsulfinyl)-indolyl enones was examined. The cycloaddition of cinnamyl and crotonyl α,β-unsaturated enones with cyclopentadiene in the presence of a lanthanoid triflate as a Lewis acid proceeds smoo

Recoverable chiral sulfoxide: remote asymmetric induction in Lewis acid-promoted Diels-Alder reaction of chiral sulfinyl-substituted pyrrolyl α,β-unsaturated enones

1-[2-(p-Tolylsulfinyl)]pyrrolyl α,β-unsaturated enones served as efficient dienophiles in the Diels-Alder reaction, where the use of aluminium chloride or a lanthanide triflate effected the cycloaddition with cyclopentadiene, affording the endo adduct with high diastereoselectivity. In particular, for the sulfinyl dienophile, the chiral auxiliary (i.e. the sulfinyl pyrrole) was recovered after use without any loss of optical purity.

DMAP-promoted racemization-free deacylation of carboxthioimide adducts: Carboxthioimide as a versatile carboxy protecting group

The DMAP-promoted deacylation of carboxthioimide adducts can be directed to form either acid or various ester protecting groups with no detectable levels of epimerization.

exo,exo-2-Amino-3-borneol-derived Oxazolidinone as a New Chiral Auxiliary for use in Asymmetric Transformations

N-Acylimides derived from exo,exo-2-amino-3-borneol when subjected to alkylation, Diels-Alder reaction, and conjugate additions afford the corresponding products with a high level of asymmetric induction, particularly in those cases of inherent poor diastereofacial selectivity.

SYNTHESIS OF ENANTIOMERICALLY PURE (5S)-4-AZA-2-OXA-6,6-DIMETHYL-7,10-METHYLENE-5-SPIRODECAN-3-ONE, A NOVEL CHIRAL OXAZOLIDIN-2-ONE FROM (-)-CAMPHENE FOR USE AS A RECYCLABLE CHIRAL AUXILIARY IN ASYMMETRIC TRANSFORMATIONS

By an intramolecular nitreno-mediated route (-)-camphene is transformed into a novel spiro-oxazolidin-2-one whose efficiency as a chiral auxiliary is highlighted by the excellent levels of chiral induction attained in an array of asymmetric transformations such as the Diels-Alder, conjugate addition, aldol condensation, alkylation and acylation reactions.

Stereocontrolled Diels-Alder Reactions with Chiral Tricyclic Oxazolidinones

(1R,2R,6S,7S)-5-Aza-1,10,10-trimethyl-3-oxatricyclo2,6>decan-4-one (endo-oxazolidinone) and (1R,2R,6R,7S)-isomer (exo-oxazolidinone) are found to be efficient diastereomeric auxiliaries for Diels-Alder reactions, which are promoted by L