93643-53-9

Upstream product

• 13735-81-4 1-styrenyloxytrimethylsilane 
• 123-72-8 butyraldehyde 
• 93643-58-4 (4S,5R)-2,4-Dimethyl-2,5-diphenyl-oxazolidine 
• 98-86-2 acetophenone 
• 57548-41-1 3-hydroxy-1-phenylhexan-1-one 

Relevant academic research and scientific papers

Kinetic Resolution of β-Hydroxy Carbonyl Compounds via Enantioselective Dehydration Using a Cation-Binding Catalyst: Facile Access to Enantiopure Chiral Aldols

A practical and highly enantioselective nonenzymatic kinetic resolution of racemic β-hydroxy carbonyl (aldol) compounds through enantioselective dehydration process was developed using a cation-binding Song's oligoethylene glycol (oligoEG) catalyst with p

Direct asymmetric aldol reaction of acetophenones with aromatic aldehydes catalyzed by chiral Al/Zn heterobimetallic compounds

Chiral Al/Zn heterobimetallic complexes are effective catalysts for the direct highly enantioselective aldol reaction of acetophenones with aromatic aldehydes. The Al site in the complex acts as a Lewis acid to activate aldehyde, whereas ethylzinc alkoxide plays a role of a Br?nsted base to form a reactive zinc enolate with acetophenone. Distinct nature of two different metals contributes to the efficient direct asymmetric aldol reaction.

Investigations of enantioreversal in both direct and directed enantioselective aldol reactions catalyzed by CuCl2[(-)-sparteine] and NiCl2[(-)-sparteine] complexes

The use of structurally well-defined chiral [CuCl2(sparteine)] 1 and [NiCl2(sparteine)] 2 complexes as catalysts under fluoride anion-promoted double catalytic activation (DCA) conditions cause enantioreversal in the asymmetric Mukaiyama aldol reaction of 1-phenyl-1-trimethylsiloxyethylene with various aromatic aldehydes. A similar enantioreversal also occurs in the direct aldol reaction between methyl vinyl ketone and various aromatic aldehydes under Et3N promoted DCA conditions. We have quantitatively analyzed using group theoretical analysis via symmetry deformation coordinates, the molecular structures of 1 and 2 from the X-ray structural data; the results from the study show that the innate stereochemical differences that are present in their molecular structures, form the basis for the enantioreversal phenomenon in the asymmetric C-C bond-forming aldol reactions.

Direct asymmetrie aldol reaction of aryl ketones with aryl aldehydes catalyzed by chiral BINOL-derived zincate catalyst

(Chemical Equation Presented) Direct asymmetric aldol reaction of aryl ketones with aryl aldehydes catalyzed by chiral metal complex is reported for the first time herein. Two novel semicrown chiral ligands 1a and 1b were synthesized from (S)- and (R)-BIN

A novel strategy for the convergent synthesis of 1,3,5,...-polyols: Enone formation, asymmetric dihydroxylation, reductive cleavage, hydride addition

Asymmetric dihydroxylation of α,β-unsaturated ketones provided α,β-dihydroxyketones with up to 100% ee. The Cα-O bond of these intermediates or their bis-TMS ethers, acetonides, phenylborates or orthoformiates was cleaved with SmI2, affording β-hydroxyketones. The latter can be reduced to furnish syn- or anti-configured 1,3-diols of any desired configuration. Georg Thieme Verlag Stuttgart.

Enantioselective Mukaiyama-aldol and aldol-dihydropyrone annulation reactions catalyzed by a tryptophan-derived oxazaborolidine

The (S)-tryptophan derived catalyst 1, has been used to effect enantioselective Mukaiyama-aldol and aldol-dihydropyrone annulation reactions of trimethylsilyloxy olefins and dienes.

HIGHLY ENANTIOSELECTIVE ALDOL REACTION OF METHYL KETONES VIA CHIRAL STANNOUS AZAENOLATES

Chiral 1,3-oxazolidines are readily prepared from methyl ketones and chiral norephedrine.Formation of stannous azaenolates from the oxazolidines and reaction with aldehydes followed by removal of the chiral auxiliary lead to the aldol products in high level of enantiomeric putity.