222845-31-0

Upstream product

• 593288-68-7 (S)-3-(4-methylphenyl)butyl 4-methyl-1-benzenesulfonate 
• 130633-06-6 (E)-3-(4-methylphenyl)-but-2-en-1-ol 
• 151765-65-0 (S)-3-(4-methylphenyl)butanal 
• 1504-75-2 3-(4-methylphenyl)acrylaldehyde 
• 1461-10-5 (S)-3-(4-methylphenyl)-1-butanol 

Downstream Products

• 1786-15-8 (S,E)-nuciferol 
• 3649-81-8 (S)-curcumene 

Relevant academic research and scientific papers

Catalytic enantioselective β-alkylation of α,β-unsaturated aldehydes by combination of transition-metal- and aminocatalysis: Total synthesis of bisabolane sesquiterpenes

Branching out! The first co-catalytic enantioselective (up to 98:2 e.r.) β-alkylation of α,β-unsaturated aldehydes by combination of simple chiral amine and copper catalysts provides β-branched aldehydes in a one-pot protocol (see scheme). The methodology was applied to the short total syntheses of bisabolane sesquiterpenes (S)-(+)-curcumene, (E)-(S)-(+)-3- dehydrocurcumene and (S)-(+)-tumerone.

Baker's yeast mediated enantioselective synthesis of the bisabolane sesquiterpenes curcumene, turmerone, dehydrocurcumene and nuciferal

Fermenting baker's yeast converts the allylic alcohol 6 into enantiomerically pure (S)-(+)-3-(p-tolyl)butan-1-ol 7 which is a useful chiral building block for the synthesis of bisabolane sesquiterpenes. The versatility of this approach is shown in the preparation of (S)-(+)-curcumene, (S)-(+)-turmerone, (S)-(+)-dehydrocurcumene and (E,S)-(+)-nuciferal.