89358-17-8

Upstream product

• 79786-73-5 1-chloromethyl-1-phenylbut-3-en-1-ol 
• 532-27-4 1-chloroacetophenone 
• 6337-34-4 2,2-dimethyl-5-phenyl-1,3-dioxolan-4-one 
• 129286-24-4 5-allyl-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-one 

Downstream Products

• 110577-92-9 (S)-(-)-2-phenyl-pent-4-ene-1,2-diol 
• 4743-74-2 (S)-(-)-2-phenyl-4-penten-2-ol 
• 4743-74-2 (R)-2-phenyl-pent-4-en-2-ol 

Relevant academic research and scientific papers

Lipase AKG mediated resolutions of α,α-disubstituted 1,2-diols in organic solvents; remarkably high regio- and enantio-selectivity

Diols 1, which contain adjacent tertiary and primary hydroxy groups, can be selectively mono-acylated at the primary hydroxy group by many lipases in organic solvents. Since the reaction does not take place at the chiral tertiary centre itself, observed enantioselectivities are usually low. Only the combination of one lipase, lipase AKG (Amano, Pseudomonas sp.), with selected substrates gives high enantioselectivities (E 20 to > 200). Also, the solvent and acyl donor employed influences the outcome. On the basis of the results of lipase AKG towards substrates 1 an active site model for this specific lipase has been developed, which can account for the results obtained. Full experimental details on the synthesis of diols 1 and enzymatic preparation of acetates 2 are given. Also, the absolute stereochemistry of the enzymatically prepared diols 1 has been established by independent synthesis from (R)-mandelic acid.

β-Substituted Organolithium Compounds from Chlorohydrins: Application to the Direct Synthesis of Bifunctionalized Organic Cpmpounds

The reaction of different chlorohydrins with n-butyl-lithium at -78 deg C followed by metallation wiht lithium naphthalenide at the same temperature leads to very reactive organolithium compounds bearing an alkoxide function at the β-position with respect to metal.The reaction of these intermediates with several electriphiles leads to mono- as well as bi-functionalized organic compounds.Thus, treatment of these dianions with deuterium oxide, oxygen, carbon dioxide, benzyl bromide, dimethyl disulphide, and carbonyl compounds, gave 2-deuterioalcohols, 1,2-diols, β-hydroxy-acids, 2-benzyl alcohols, 2-hydroxy-thioethers, and 1,3-diols respectively.The preparation of β-substituted organolithium derivatives can be alternatively carried out starting from α-chloroketones by the same procedure.When the lithium atom is linked to a secondary carbon atom the dianions are very unstable and decompose, even at -100 deg C, by β-elimination yielding the corresponding olefins.