110549-79-6

Upstream product

• 82188-39-4 (3R,4R)-(+)-1,6-dibromohexane-3,4-diol 
• 1069-23-4 (3R,4R)-1,5-hexadiene-3,4-diol 
• 13269-52-8 trans-3-Hexene 
• 4437-51-8 3,4-hexanedione 
• 22520-19-0 trans-hexane-1,2-diol 
• 219527-99-8 O¹,O²,O⁵,O⁶-tetrakis-(toluene-4-sulfonyl)-D-mannitol 
• 98-88-4 benzoyl chloride 
• 4468-66-0 2,3-diethyloxirane 
• 592-47-2 3-hexene 
• 108-24-7 acetic anhydride 
• 97-72-3 2-Methylpropionic anhydride 
• 116297-02-0 (4S)-4-hydroxyhexan-3-one 
• 64-19-7 acetic acid 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 509150-88-3 (3R,4R)-4-(4-Methoxy-benzyloxy)-hexan-3-ol 

Relevant academic research and scientific papers

Ligand-based improvement of enantioselectivity in the catalytic asymmetric dihydroxylation of dialkyl substituted olefins

A high level of asymmetric induction was achieved in the asymmetric dihydroxylation of dialkyl substituted olefins using 9-O-aryldihydroquinidines as ligands.

Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedione

In this paper we have studied the liquid-phase enantioselective hydrogenation of 3,4-hexanedione using Pt-based catalysts, modified with chiral organotin compounds derived from the (-)-menthyl group: (-)-Pt-MenSnBu 3 and (-)-Men3Sn-Sn-(-)-Men3. The organotin chiral modifiers were carefully synthesized and characterized in order to obtain optically pure compounds. The catalysts were prepared through a controlled surface reaction between the supported transition metal and the organometallic compound, using techniques derived from Surface Organometallic Chemistry on Metals (SOMC/M). The organobimetallic catalytic systems were found to be active and enantioselective in the hydrogenation of 3,4-hexanedione, yielding an enantiomeric excess of 25-27% for 4-hydroxy-3-hexanone.

Structural Study of Bromide-Bridged Pd Chain Complex with Weak CH···O Hydrogen Bonds

A novel Br-bridged Pd chain complex, [Pd(hxn)2Br](TsO)2 (2) (TsO– = p-toluenesulfonate), was synthesized from a new in-plane ligand (3S,4S)-3,4-diaminohexane (hxn). 2 forms PdII/PdIV mixed-valence state, as confirmed by single-crystal X-ray structure analysis and polarized Raman spectra. The hxn ligand provides the additional hydrogen bonds (CH···O) between the methyl group of the ligands and the O atoms of TsO– anions, which are weaker than those observed in the chain complex with hydroxy group, [Pd(dabdOH)2Br]Br2 (1).

Assessing the stereoselectivity of: Serratia marcescens CECT 977 2,3-butanediol dehydrogenase

α-Hydroxy ketones and vicinal diols constitute well-known building blocks in organic synthesis. Here we describe one enzyme that enables the enantioselective synthesis of both building blocks starting from diketones. The enzyme 2,3-butanediol dehydrogenase (BudC) from S. marcescens CECT 977 belongs to the NADH-dependent metal-independent short-chain dehydrogenases/reductases family (SDR) and catalyses the selective asymmetric reductions of prochiral α-diketones to the corresponding α-hydroxy ketones and diols. BudC is highly active towards structurally diverse diketones in combination with nicotinamide cofactor regeneration systems. Aliphatic diketones, cyclic diketones and alkyl phenyl diketones are well accepted, whereas their derivatives possessing two bulky groups are not converted. In the reverse reaction vicinal diols are preferred over other substrates with hydroxy/keto groups in non-vicinal positions.

DOCUMENTING THE SCOPE OF THE CATALYTIC ASYMMETRIC DIHYDROXYLATION

A wide variety of functionalized and unfunctionalized olefins are efficiently converted to the corresponding cis vicinal diols in moderate to good enantiomeric excess via the "slow addition" enhanced catalytic asymmetric osmylation process.

On the Mechanism of Osmium Catalyzed Asymmetric Dihydroxylation (ADH) of Alkenes

Dihydroquinidine and dihydroquinine bisesters of malonic acid, adipic acid and terephthalic acid are used as chiral auxiliaries for osmium tetroxide catalyzed asymmetric dihydroxylation of alkenes.Highly stereoselective osmylation of alkenes has been rationalized on the basis of ?-? interaction of the alkenes with the ligand.

Asymmetric hydrogenation of 3,4-hexanedione over PtSn catalysts

In this work, some results of the liquid-phase racemic and enantioselective hydrogenation of 3,4-hexanedione are presented. The catalysts employed were platinum-based, supported on SiO2. Monometallic catalysts were modified with organotin precu

Highly enantioselective dihydroxylation of olefins by osmium tetroxide with chiral diamines

Enantioselective dihydroxylation of olefins by osmium tetroxide with chiral diamines was examined. The hydroxylation employing 1 gave exceptionally high optical yields in the production of diols from mono-, trans-di-, and trisubstituted olefins. Virtually complete asymmetric induction was observed in the reaction of trans-β-methylstyrene. The stereochemical outcome of the asymmetric reaction strongly suggested that the oxidation proceeded via organometallacycle 14.

Synthesis of chiral nonracemic diols via nucleophilic opening of (S,S)-1,2,3,4-diepoxybutane

(S,S)-1,2,3,4-diepoxybutane was synthesized from (R,R)-dimethyl tartrate. Nucleophilic opening of this diepoxybutane gave a convenient method for generating a variety of chiral nonracemic diols.

Asymmetric Dihyroxylation of Alkenes with Osmium Tetroxide: Chiral N,N'-Dialkyl-2,2'-bipyrrolidine Complex

Asymmetric osmylation of alkenes by using N,N'-dialkyl-2,2'-bipyrrolidines as the chiral ligands shows a high asymmetric induction and a marked dependence of the enantioselectivity on both the N-alkyl group and the reaction solvent.