356793-34-5

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 81114-98-9 Chan's diene 
• 152203-66-2 (E)-(S)-4-Phenyl-but-3-ene-1,2-diol 
• 152203-65-1 (4S)-2,2-dimethyl-4-styryl-1,3-dioxolane 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 931094-47-2 (E)-(R)-3-Oxo-7-phenyl-5-trimethylsilanyloxy-hept-6-enoic acid methyl ester 
• 96-32-2 bromoacetic acid methyl ester 
• 132203-22-6 (R,E)-3-hydroxy-5-phenylpent-4-enenitrile 

Downstream Products

• 500-64-1 Kavain 
• 173654-23-4 (R)-6-((E)-Styryl)-dihydro-pyran-2,4-dione 

Relevant academic research and scientific papers

A new procedure for the enantioselective vinylogous aldol reaction of Chan's diene

Chiral δ-hydroxy-β-ketoesters are easily available through the enantioselective vinylogous aldol reaction of Chan's diene promoted by a SiCl4/chiral phosphoramide catalytic system. The procedure is conveniently exploited for a very rapid approach to (+)-kavain, a natural bio-active α-pyrone compound.

Total synthesis of (R)-(+)-kavain via (MeCN)2PdCl 2-catalyzed isomerization of a cis double bond and sonochemical Blaise reaction

From the chiral source 2,3-O-isopropylidene-D-glyceraldehyde 2, the natural product (R)-(+)-kavain 1a was efficiently synthesized in a total yield of 25% via (MeCN)2PdCl2-catalyzed isomerization of the cis double bond of an olefin as the key step and sonochemical Biaise reaction. The chiral center adjacent to the cis double bond was retained without protection of the free allylic hydroxy during the isomerization process. Georg Thieme Verlag Stuttgart.