39149-97-8

Upstream product

• 2381-87-5 4-methyl-5,6-dihydro-2H-pyran-2-one 
• 53358-18-2 (Z)-2-methyl-pentenedioic acid diethyl ester 
• 67116-19-2 3-methyl-pentenedioic acid anhydride 
• 52313-87-8 3-methyl-2-pentene-1,5-diacid dimethyl 
• 372-42-9 3-methylpent-2-enedioic acid 
• 674-26-0 mevalonolactone 
• 53120-74-4 3,3-dimethylpent-1,5-diol 
• 763-32-6 2-methyl-1-buten-4-ol 
• 50-00-0 formaldehyd 
• 10021-22-4 3,6-dihydro-4-methyl-2H-pyran-2-one 
• 115-11-7 isobutene 

Downstream Products

• 922-62-3 3-Methyl-cis-2-penten 
• 133545-68-3 3,3-dimethyl-2(cis-3-methyl-5-bromo-2-ene)pentyl cyclohexanone 

Relevant academic research and scientific papers

Quaternary Stereogenic Centers through Enantioselective Heck Arylation of Acyclic Olefins with Aryldiazonium Salts: Application in a Concise Synthesis of (R)-Verapamil

We describe herein a highly regio- and enantioselective Pd-catalyzed Heck arylation of unactivated trisubstituted acyclic olefins to provide all-carbon quaternary stereogenic centers. Chiral N,N ligands of the pyrimidine- and pyrazino-oxazoline class were developed for that purpose, providing the desired products in good to high yields with enantiomeric ratios up to >99:1. Both linear and branched substituents on the olefins were well-tolerated. The potential of this new method is demonstrated by the straightforward synthesis of several O-methyl lactols and lactones containing quaternary stereocenters, together with a concise enantioselective total synthesis of the calcium channel blocker verapamil.

Facile synthesis of anhydromevalonolactone from ethyl acetoacetate

Ethyl acetoacetate was transformed to 3-methylglutaconic anhydride, which upon LAH reduction and Jones oxidation afforded anhydromevalonolactone.

SYNTHESIS OF (+/-)-α-CHAMIGRENE

Regiospecific spiroalkylation of the selectively generated enolate arising from the 1,4-addition of lithium dimethylcuprate to 3-methylcyclohex-2-en-1-one allows an efficient preparation of spiroketones, including a key intermediate for the synthesis of (+/-)-α-Chamigrene.

DIMETHYLALUMINUM CHLORIDE CATALYZED ENE REACTIONS OF ALDEHYDES.

Dimethylaluminum chloride, which is a mild Lewis acid and a proton scavenger, catalyzes the ene reactions of aliphatic and aromatic aldehydes with alkenes containing a disubstituted vinylic carbon. Proton-initiated rearrangements do not occur, since the alcohol-Lewis acid complex formed in the ene reaction reacts rapidly to give methane and a nonacidic aluminum alkoxide. Formaldehyde and excess Me//2AlCl give good yields of ene adducts with all types of alkenes. With 1 equiv of Me//2AlCl, formaldehyde and mono- and 1,2-disubstituted alkenes give gamma -chloro alcohols resulting from cis addition of chlorine and hydroxymethyl groups to the double bond. This work is pertinent to the synthesis of alcohols.