130814-75-4

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 130814-73-2 (E)-(1'R)-2-Methyl-3-(1'-phenylethoxy)-propenal 
• 19493-09-5 Methylenetriphenylphosphorane 
• 473733-71-0 (+)-(E)-2-methyl-3-((S)-1-phenylethoxy)prop-2-enal 
• 1445-91-6 (S)-1-phenylethanol 
• 1517-69-7 (R)-1-phenylethanol 

Downstream Products

• 130814-80-1 (3aS,4R,7aS)-5-Methyl-4-((R)-1-phenyl-ethoxy)-3a,4,7,7a-tetrahydro-isobenzofuran-1,3-dione 
• 130846-99-0 (1S,2S,6R)-1,6,7,7-Tetrachloro-3-methyl-2-((R)-1-phenyl-ethoxy)-bicyclo[4.1.0]hept-3-ene 
• 130814-77-6 (S)-6-Methyl-2-phenyl-5-((R)-1-phenyl-ethoxy)-5,8-dihydro-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione 
• 130814-82-3 (1S,4aS,9aS)-2,9a-Dimethyl-1-((R)-1-phenyl-ethoxy)-1,4,4a,9a-tetrahydro-anthraquinone 
• 130814-84-5 1,4,4a,9a-Tetrahydro-8-hydroxy-2-methyl-1-(1-phenylethoxy)-9,10-anthraquinone 
• 130814-85-6 1-[(1S,5R)-4-Methyl-5-((R)-1-phenyl-ethoxy)-cyclohex-3-enyl]-ethanone 
• 130814-79-8 (4aR,5S,8aS)-2,3-Dichloro-6-methyl-1,4-dioxo-5-((R)-1-phenyl-ethoxy)-1,4,5,8-tetrahydro-naphthalene-4a,8a-dicarbonitrile 
• 130814-86-7 (1R,2S,3R)-4-Methyl-3-((R)-1-phenyl-ethoxy)-cyclohex-4-ene-1,2-dicarboxylic acid diethyl ester 
• 130814-83-4 (1R,4aS,9aS)-2-Methyl-1-((R)-1-phenyl-ethoxy)-1,4,4a,9a-tetrahydro-anthraquinone 
• 746-47-4 tetrabenzo[5.5]fulvalene 
• 2071-44-5 di-fluoren-9-ylidene-hydrazine 
• 130814-93-6 (1R,2S,3S)-3-Hydroxy-4-methyl-cyclohex-4-ene-1,2-dicarboxylic acid 
• 130814-93-6 (1S,2S,3S)-3-Hydroxy-4-methyl-cyclohex-4-ene-1,2-dicarboxylic acid 
• 130814-92-5 1-((1S,5S)-5-Hydroxy-4-methyl-cyclohex-3-enyl)-ethanone 

Relevant academic research and scientific papers

Enantioselective Terpene Syntheses by Diels-Alder Reaction of 1-(1-Arylalkoxy)-2-methyl-1,3-butadiene with Isoprene

The (R)- and (S)-1-(1-arylalkoxy)-2-methyl-1,3-butadienes 6 undergo cycloadditions with excess isoprene (7) under pressure to yield not only the expected (4S,6R)- and (4R,6S)-trans-carveol (8) with up to 96percent e.e. but also up to 40percent of (R)- and (S)-limonene (9) with up to 93percent e.e.Asymmetric induction is proposed to arise from a transition state involving definite ? stacking of one molecule of isoprenyl ether and two molecules of isoprene.Key Words: (4S,6R)-, (4R,6S)-trans-Carveol / (R)-, (S)-Limonene / Isoprene / Isoprenyl ether / Cycloaddition, diastereo-, enantioselective

Asymmetric Diels-Alder Reactions with Chiral 2-Methyl-1-(1-arylethoxy)-1,3-butadienes

Chiral 1-arylethanols 2, prepared by enantioselective reduction of phenones 1 with lithium aluminium hydride and Chirald , are converted to the chiral 2-methyl-1-(1-arylethoxy)-1,3-butadienes 5 by vinylogous transesterification with 2-methyl-1-ethoxyacrolein (3) and subsequent Wittig methylenation of the intermediate chiral 3-(1-arylethoxy)-2-methylacroleins 4.The 1-arylethyl isoprenyl ethers 5 undergo cycloadditions as donor-activated 1,3-dienes with numerous electron-deficient dienophiles in good chemical yields and high diastereomeric excesses (>/= 95percent).The chiral inductor is removed optically pure from the cycloadducts by hydrogen chloride and silica gel in dichloromethane suspension at room temperature.