124338-53-0

Upstream product

• 53346-05-7 2-(benzyloxy)propanal 
• 2747-38-8 methyltrichlorotitanium 
• 917-54-4 methyllithium 
• 75-16-1 methylmagnesium bromide 
• 113133-46-3 3-(phenylmethoxy)butan-2-one 
• 185961-43-7 4-Nitro-benzoic acid (1S,2R)-2-benzyloxy-1-methyl-propyl ester 
• 100-52-7 benzaldehyde 
• 100-39-0 benzyl bromide 
• 75281-80-0 4,5-dimethyl-2-phenyl-(2α,4α,5β)-1,3-dioxolane 
• 124338-52-9 (2R,3R)-3-(phenylmethoxy)-2-butanol 
• 271578-41-7 (1R,4S,5R,6R)-5-[(S)-((1S,2R)-2-Benzyloxy-1-methyl-propoxy)-methoxy-methyl]-6-phenyl-bicyclo[2.2.1]hept-2-ene 
• 97203-22-0 (-)-(S)-3-(phenylmethoxy)-2-butanone 
• 273400-78-5 (4R,5S)-4,5-dimethyl-2-phenyl-1,3-dioxolane 

Downstream Products

• 170985-78-1 [2-((1S,2R)-2-Benzyloxy-1-methyl-propoxymethoxy)-ethyl]-trimethyl-silane 

Relevant academic research and scientific papers

Asymmetric Induction by a Nitrogen14N/15N Isotopomer in Conjunction with Asymmetric Autocatalysis

Chirality arising from isotope substitution, especially with atoms heavier than the hydrogen isotopes, is usually not considered a source of chirality in a chemical reaction. An N2,N2,N3,N3-tetramethyl-2,3-butan

Hydroxylated analogues of the orally active broad spectrum antifungal, Sch 51048 (1), and the discovery of posaconazole [Sch 56592; 2 or (S,S)-5]

As part of a detailed study, the syntheses, biological activities, and pharmacokinetic properties of hydroxylated analogues of the previously described broad spectrum antifungal agents, Sch 51048 (1), Sch 50001 (3), and Sch 50002 (4), are described. Based on an overall superior profile, one of the alcohols, Sch 56592 (2), was selected for clinical studies.

Reductive cleavage of acetals and ketals with 9-borabicyclo[3.3.1]nonane

The reductive cleavage of benzaldehyde acetals and acetophenone ketals with the air-stable crystalline 9-borabicyclo[3.3.1]-nonane dimer provides monobenzylated ether derivatives of diols and 1,2-oxygen-transposed β-phenethyl alcohols, respectively. The boron moiety is effectively recovered through simple procedures which involve convenient air-stable reagents and boron byproducts. The process is particularly selective for 1,3-diols giving the more substituted monobenzyl ether derivatives exclusively. With acetophenone ketals both reduction and elimination occur, permitting 9-BBN-H to hydroborate the resulting styrene to produce 1,2-oxygen-transposed β-phenethyl alcohols cleanly. Potential applications of this new process were illustrated with the synthesis of the hallucinogen, mescaline, and the analgesic, ibufenac.

Diastereoselectivity in the reduction of α-oxy- and α-amino-substituted acyclic ketones by polymethylhydrosiloxane

Diastereoselectivity in the reduction of α-alkoxy-, α-acyloxy-, and α-alkylamino-substituted ketones with polymethylhydrosiloxane (PMHS) in the presence of fluoride ion catalysis was investigated. High syn-selectivity was observed in the reduction of α-alkoxy, α-acyloxy, and α-dialkylamino ketones. Reduction of α-monoalkylamino ketone proceeded in anti-selective manner with moderate selectivity. The observed selectivity is explained based on Felkin-Anh and Cram-chelate models.

Hydrogenation of α-Keto Ethers: Dynamic Kinetic Resolution with a Heterogeneous Modified Catalyst and a Heterogeneous Base

The first successful example of the asymmetric hydrogenation of substituted α-keto ethers with Cinchona-modified Pt/Al2O3 is reported. In the absence of an additional base, kinetic resolution of the racemic starting material was observed with high diastereoselectivity and ee's up to 98% at conversions of a strong reaction acceleration but racemic product. Immobilization of OH- on solid ion exchangers resulted in the desired dynamic kinetic resolution, and ee's of >80% were obtained at >95% conversion. These effects are rationalized on the basis of a simple kinetic and structural model.

Chiral oxazaborolidinone-mediated enantioselective ring-cleavage reaction of a mixture of diastereomeric 1,3-dioxolane acetals: Application to asymmetric desymmetrization of meso-1,2-diols

Ring-cleavage reaction of a mixture of diastereomeric dioxolane acetals syn- and anti-1b-e proceeds in an enantiodifferentiating manner in the presence of chiral Lewis acid 2. The reaction is utilized as a key step in asymmetric desymmetrization of meso-1,2-diols.

Optical resolution of racemic norbornene aldehydes: Kinetically controlled intramolecular haloetherification of ene acetals

Haloetherification reaction of a diastereomeric mixture of the ene acetals 2 and 2', derived from racemic norbornene aldehydes and chiral non- racemic (S,S)-hydrobenzoin, proceeded in a kinetically controlled manner to give the optically pure aldehydes 3 along with the intact ene acetals 2'. Compounds 3 and 2' were converted to the optically pure norbornene aldehydes in both enantiomeric forms. Then a new chiral auxiliary for asymmetric desymmetrization of meso-1,2-diols was found. (C) 2000 Elsevier Science Ltd.

Desymmetrization of meso-1,2-diols via chiral oxazaborolidine-mediated ring-cleavage of acetal derivatives with silyl ketene S,O-acetal

Desymmetrization of meso-1,2-diols leading to enantiomerically enriched MOM and MEM ethers is realized via chiral oxazaborolidine-mediated enantioselective ring-cleavage reaction of the acetal derivatives with silyl ketene S,O-acetal.

Chelation-controlled reduction of α- and β-oxygenated ketones with lithium tri-n-butylborohydride

Lithium tri-n-butyl borohydride showed high selectivity in the reduction of α- and β-oxygenated ketones, giving a preponderance of the chelation controlled products.

Methylaluminum bis(4-substituted-2,6-di-tert-butylphenoxide) as an efficient nonchelating Lewis acid: Application to asymmetric Diels-Alder reaction and diastereoselective alkylation to alkoxy carbonyl substrates

The exceptionally bulky methylaluminum bis(4-substituted-2,6-di-tert-butylphenoxide) such as MAD or MABR can be successfully utilized as a highly efficient nonchelating Lewis acid for achieving high stereoselectivity in 1,n asymmetric induction in cyclic