90819-99-1

Upstream product

• 15082-42-5 lithium benzyloxide 
• 90719-39-4 (4R,5S)-3-((3'S,4'S,5'R,6'R)-5-methylbicyclo<2.2.1>heptene-4'-carbonyl)-4-methyl-5-phenyl-2-oxazolidinone 
• 100-51-6 benzyl alcohol 
• 188608-83-5 (1S,2R,3R,4R,S_S)-2-[2-(p-Tolylsulfinyl)pyrrole-1-carbonyl]-3-methylbicyclo[2.2.1]hept-5-ene 
• 331284-01-6 (4R,5S)-4-cyclohexyl-1,5-dimethyl-3-[(1S,2S,3R,4R)-3-methylbicyclo[2.2.1]hept-5-en-2-ylcarbonyl]-2-imidazolidinone 
• 331283-98-8 (4R,5S)-1,5-dimethyl-3-[(1S,2S,3R,4R)-3-methylbicyclo[2.2.1]hept-5-en-2-ylcarbonyl]-4-phenyl-2-imidazolidinone 
• 542-92-7 cyclopenta-1,3-diene 
• 623-68-7 trans-crotonic anhydride 

Relevant academic research and scientific papers

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

N-Alkenoylimidazolidin-2-ones as chiral dienophiles in Diels-Alder cycloaddition reactions

Homochiral N-enoylimidazolidin-2-ones 5-8 are readily accessible, practical, and highly diastereoselective dienophiles in dialkylaluminium-promoted Diels-Alder reactions. Acrylate, methacrylate, and (E)-crotonate derivatives bearing ephedrine-based imidaz

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.

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.

Recoverable chiral sulfoxide: Asymmetric diels-alder reaction using optically active 1-(2-p-tolylsulfinyl)pyrrolyl α,β-unsaturated ketones as a dienophile

The Diels-Alder reaction of chiral cinnamoyl-and crotonyl (2-p-tolylsulfinyl)pyrrole with cyclopentadiene in the presence of AlCl3 or Yb(OTf)3 proceeded smoothly to give the corresponding endo adducts in excellent yield with high diastereoselectivity, ranging from 92 to 99% d.e. The chiral auxiliary, 2-pyrrolesulfoxide was efficiently recovered after alcoholysis of the adduct without loss of optical purity.

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

(5R)-7,8:9,10-Di-O-isopropylidene-2,6-dioxa-4-azaspirodecan-3-one: A New Chiral Spirooxazolidin-2-one derived from D-(+)-Galactose for use in Asymmetric Transformations

Starting from D-(+)-galactose, the crystalline spirooxazolidin-2-one 2 can be readily prepared in an optically pure state by a nitrene-mediated four-step sequence, and serves to control both aldol and Diels-Alder reactions with high chiral efficiency, being easy to remove after use.