89919-52-8

Upstream product

• 269719-23-5 diethyl p-tolylsulfinylmethylphosphonate 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 89764-37-4 ethyl (-)-(Z)-(R)_s-2-methyl-3-(p-tolylsulfinyl)propenoate 
• 542-92-7 cyclopenta-1,3-diene 

Downstream Products

• 108692-16-6 ethyl (-)-(1R,4S)-exo-2-methyl-endo-3-(p-tlylthio)bicyclo<2.2.1>heptane-endo-2-carboxylate 
• 108653-79-8 (-)-(1S,4R)-endo-2-methyl-3-oxobicyclo<2.2.1>heptane-exo-2-carboxaldehyde 
• 89826-18-6 ethyl (+)-(1S,4R)-endo-2-methyl-3-(p-tolylthio)bicyclo<2.2.1>heptane-exo-2-carboxylate 
• 120410-03-9 (1R,2S,3S,4S)-2-Methyl-3-((R)-toluene-4-sulfinyl)-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

The Asymmetric Diels-Alder Cycloaddition Using Ethyl(-)-(Z)-(R)s-2-methyl-3-(p-tlylsulfinyl)propenoate: Application to an Enantioselective Synthesis of (+)-epi-β-Santalene

The Diels-Alder reaction of ethyl (-)-(Z)-(R)s-2-methyl-3-(p-tolylsulfinyl)propenoate (6) with cyclopentadiene gave the adducts, 7, 8, and 9 in a high diastereoselective manner.The cycloadduct 7 was transformed into the acetal (-)-25.The racemic 25 was used as an intermediate in the synthesis of (+/-)-β-santalol.Thus, the chiral acetal (-)-25 should provide a route to (-)-Β-santalol.The cycloadduct 8 was converted into (+)-epi-β-santalene in 11 steps.

HIGHLY DIASTEREOSELECTIVE DIELS-ALDER REACTION OF OPTICALLY ACTIVE ETHYL 2-p-TOLYLSULFINYLMETHYLENEPROPIONATE WITH CYCLOPENTADIENE

Stereochemistry of the Diels-Alder reaction of ethyl Z- and E-2-p-tolylsulfinylmethylenepropionate with cyclopentadiene has been studied.The high diastereoselectivity was observed especially in the case of exo-cycloaddition.