22658-80-6

Upstream product

• 2442-10-6 oct-1-en-3-yl acetate 
• 35926-06-8 1-butyl-2-propenyl acetate 

Downstream Products

• 1122571-39-4 methyl 4-((1S,2S)-1-hydroxy-2-vinylheptyl)benzoate 

Relevant academic research and scientific papers

Regioselective Asymmetric Allylic Alkylation Reaction of α -Cyanoacetates Catalyzed by a Heterobimetallic Platina-/Palladacycle

Allylic substitution reactions provide a valuable tool for the functionalization of CH acidic pronucleophiles. Often, control over the stereocenter generated at the nucleophilic reactant is still a challenge. The majority of studies that address this issue employ metal complexes with a low metal oxidation state (e.g. Pd0) to form allyl complexes through oxidative addition. In this article we describe the use of heterobimetallic PtII/PdII complexes, which probably activate the olefinic substrates through an SN2′ pathway. The reaction of α-cyanoacetates delivers linear allylation products with exclusive regioselectivity and high E/Z-selectivity for the new C=C double bond. Although the enantioselectivities attained are moderate, they are significantly higher than with related mono-PdII or -PtII catalysts or the corresponding bis-PdII complex, which indicates cooperation of the different metals. Control experiments suggest simultaneous activation of both reaction partners.

Atom transfer radical cyclization (ATRC) applied to a chemoenzymatic synthesis of Quercus lactones

The natural fragrances (+)-trans whisky lactone 2 and (+)-trans cognac lactone 4, together with a minor amount of their (-)-cis stereoisomers, were prepared in 50% and 42% overall yield, respectively, starting from racemic 1-hepten-3-ol (±)-5 and 1-octen-3-ol (±)-6. The procedure involved first the enantioconvergent, lipase mediated transformation of the secondary allylic alcohols derived dichloroacetates (±)-7 and (±)-8 into the corresponding homochiral (+)-7 and (+)-8, combined with their cyclization under a transition metal catalyzed atom transfer process.

Enzymic Resolution of (+/-)-Acyclic Alcohols via Asymmetric Hydrolysis of Corresponding Acetates by Microorganisms

Asymmetric hydrolysis of (+/-)-1-pentyl-2-propynyl and 1-pentyl-2-propenyl acetates by selected microorganisms produced chiral 1-octyn-3-ol and 1-octen-3-ol, respectively, with high optical purities and acetates of their antipodes.Enantioselectivity of microbial hydrolysis changed with the microorganisms used.Also, (+/-)-1-ethylhexyl acetate was asymmetrically hydrolyzed by microorganisms to give (S)-3-octanol and (R)-1-ethylhexyl acetate of relatively low optical purity and hydrolytic ratio, compared with those of (+/-)-1-pentyl-2-propynyl acetate.

Preparation of Chiral Secondary Alcohols via Enantioselective Hydrolysis of Corresponding Esters with a Microorganism

Esters of secondary alcohols were enantioselectively hydrolyzed with Brevibacterium ammoniagenes IAM 1645, ATCC 6872 to give the corresponding chiral alcohols and esters.While the esters of alkyl vinyl carbinols gave (S)-alcohols, dialkyl carbinol esters were hydrolyzed to (R)-alcohols of rather low optical purities.Hydrolysis of α-phenethyl acetate proceeded smoothly resulting in the formation of (R)-α-phenethyl alcohol in good optical yield.The structure of the acyl moiety of 1-tridecen-3-yl esters seriously influenced the rate and optical yield of the reaction, and the acetate was found to give the best results.