94800-94-9

Upstream product

• 1008-76-0 4,5-dihydro-5-phenyl-2(3H)-furanone 
• 74-95-3 1,1-dibromomethane 
• 104089-17-0 ethyl 4-(iodozincio)butanoate 
• 100-52-7 benzaldehyde 
• 533-68-6 2-bromobutyric acid ethyl ester 
• 73172-56-2 ethyl 4-benzoylbutanoate 
• 7425-53-8 ethyl 4-iodobutyrate 
• 1173997-10-8 ethyl 4-((1-phenyl-1H-tetrazol-5-yl)sulfonyl)butanoate 
• 22768-07-6 (E)-ethyl 5-phenylpent-4-enoate 
• 5205-39-0 ethyl glutaroyl chloride 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 94800-94-9 (R)-ethyl 5-hydroxy-5-phenylpentanoate 

Relevant academic research and scientific papers

Rhodium-catalyzed asymmetric hydroboration of γ,δ-unsaturated amide derivatives: δ-borylated amides

γ,δ-Unsaturated amides in which the alkene moiety bears an aryl or heteroaryl substituent undergo regioselective rhodium-catalyzed δ-borylation by pinacolborane to afford chiral secondary benzylic boronic esters. The results contrast the γ-borylation of γ,δ-unsaturated amides in which the disubstituted alkene moiety bears only alkyl substituents; the reversal in regiochemistry is coupled with a reversal in the sense of π-facial selectivity.

Stereodivergent preparation of valuable γ- Or δ-hydroxy esters and lactones through one-pot cascade or tandem chemoenzymatic protocols

A series of enantiopure hydroxy esters and lactones has been synthesized in a chemodivergent manner via alcohol dehydrogenase (ADH) reduction of the corresponding keto esters by means of cascade or tandem protocols. Thus, ADH from Rhodococcus ruber (ADH-A) or Lactobacillus brevis (LBADH) afforded both antipodes in a very selective way when dealing with small derivatives. With bulkier substrates, ADH from Ralstonia sp. (RasADH) was successfully employed to achieve the synthesis of enantioenriched γ- or δ-hydroxy esters. To isolate the corresponding lactones, two different approaches were followed: a cascade reaction by spontaneous cyclization of the hydroxy ester intermediate, or a one-pot two-step tandem protocol. Moreover, a chemoenzymatic route was designed to obtain a chiral brominated lactone, which enabled further modifications in a sequential fashion by Pd-catalyzed reactions, affording relevant functionalized lactones.

Remote ester group leads to efficient kinetic resolution of racemic aliphatic alcohols via asymmetric hydrogenation

A highly efficient method for kinetic resolution of racemic aliphatic alcohols without conversion of the hydroxyl group has been realized; the method involves hydrogenation mediated by a remote ester group and is catalyzed by a chiral iridium complex. This powerful, environmentally friendly method provides chiral δ-alkyl-δ-hydroxy esters and δ-alkyl-1,5-diols in good yields with high enantioselectivities even at extremely low catalyst loading (0.001 mol %).

Zinc metal-promoted cross-coupling reaction of non-activated alkyl halides with aldehydes in the presence of chlorotrimethylsilane

Treatment of non-activated alkyl halides 1 with aldehydes 3 in the presence of zinc metal and chlorotrimethylsilane (TMSC1), DMA and/or NMP in THF brought about highly facile and effective cross-coupling to give the corresponding alcohols in good yield. These reactions are assumed to proceed through zinc reagent intermediates generated in situ.

Selective synthesis of substituted benzylic alcohols from aromatic substrates included in β-cyclodextrin

The regio- and enantioselective reduction of substituted styrenic epoxides and aromatic ketones by borohydride in the presence of β-cyclodextrin is described. The regioselectivity is related to the hydrophobicity of the substrate, which governs its penetration inside the cavity of the cyclodextrin and is favorable to the β-opening of the epoxide. The stereoselectivity observed during the reduction is mainly dependent on the non-covalent interactions between the upper rim of the cyclodextrin and the substrate included in it. The chimioselectivity observed during the reduction of ketoester is assumed to be dependent on an alkoxyborohydride intermediate formed in the first step of the reaction. Elsevier.

A cobalt-phosphine complex as mediator in the formation of carbon-carbon bonds

The tetrakis(trimethylphospine)cobalt(0) complex, [Co{P(CH3)3}4], in either stoichiometric or catalytic amounts, was shown to be an efficient mediator for a one-pot Reformatsky-type reaction between activated halogen derivatives (esters, amides, lactones) and carbonyl compounds (aldehydes, ketones) to produce a variety of alcohols.

Preparation of Functionalized Dialkylzinc Reagents via an Iodine-Zinc Exchange Reaction. Highly Enantioselective Synthesis of Functionalized Secondary Alcohols

Functionalized dialkylzincs are obtained by the reaction of polyfunctional alkyl iodides with Et2Zn in excellent yield.Their treatment with aldehydes, in the presence of the titanium catalyst 6, affords functionalized secondary alcohols with high enantios