303142-80-5

Upstream product

• 3587-60-8 Benzyloxymethyl chloride 
• 303142-79-2 (S)-4-Isopropyl-3-((E)-2-methyl-oct-2-enoyl)-oxazolidin-2-one 
• 97961-67-6 (E)-2-methyloct-2-enoic acid 
• 5162-56-1 E-methyl-2-octen-2-oate de methyle 
• 303142-78-1 β-(n-pentyl)methacryloyl chloride 
• 66-25-1 hexanal 

Downstream Products

• 303142-84-9 (R)-1-Benzyloxy-2-(2-ethyl-[1,3]dioxolan-2-yl)-2-methyl-octane-3,4-dione 
• 391612-32-1 (R)-1-Benzyloxy-2-(2-ethyl-[1,3]dioxolan-2-yl)-2-methyl-octane-3,4-diol 
• 303142-83-8 2-((E)-(S)-1-Benzyloxymethyl-1-methyl-hept-2-enyl)-2-ethyl-[1,3]dioxolane 
• 303142-75-8 (S)-4-Benzyloxymethyl-4-methyl-decane-3,5,6-trione 
• 303142-74-7 (S)-2-((benzyloxy)methyl)-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-dione 
• 303142-82-7 (E)-(S)-4-Benzyloxymethyl-4-methyl-dec-5-en-3-one 
• 303142-86-1 (E)-(S)-4-Benzyloxymethyl-4-methyl-dec-5-en-3-ol 
• 302812-60-8 (E)-(S)-2-Benzyloxymethyl-2-methyl-oct-3-enal 
• 303142-81-6 (E)-(R)-2-Benzyloxymethyl-2-methyl-oct-3-en-1-ol 

Relevant academic research and scientific papers

Novel stereoselective construction of a quaternary carbon: Application to synthesis of the cyclopentenedione moiety of madindolines

Enantioselective synthesis of the cyclopentenedione moiety of madindolines was achieved. Stereoselective construction of a quaternary carbon was realized by alkylation of an enolate possessing chiral auxiliary. Cyclopentenedione was derived from a triketone precursor by intramolecular condensation. (C) 2000 Elsevier Science Ltd.

1,3-Rearrangement of ketene-N,O-acetals

Ketene N,O-acetals were prepared stereoselectively and submitted to a Lewis acid-mediated 1,3-rearrangement to afford C-alkylated products. The reactions proceeded in a stereoselective manner to construct a chiral quaternary carbon in high selectivity. The stereochemistry of the quaternary center was found to be opposite to that obtained by an anionic direct dienolate alkylation.