220983-58-4

Upstream product

• 696-62-8 para-iodoanisole 
• 2914-69-4 (S)-(-)-3-butyn-2-ol 
• 81532-80-1 4-(4-methoxyphenyl)-3-butyn-2-one 
• 60512-57-4 1-(2,2-dibromovinyl)-4-methoxybenzene 
• 768-60-5 4-methoxyphenylacetylen 
• 123-11-5 4-methoxy-benzaldehyde 
• 865266-03-1 4,5-Dichloro-2-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-benzoic acid (S)-3-(4-methoxy-phenyl)-1-methyl-prop-2-ynyl ester 

Relevant academic research and scientific papers

A boron-oxygen transborylation strategy for a catalytic midland reduction

The enantioselective hydroboration of ketones is a textbook reaction requiring stoichiometric amounts of an enantioenriched borane, with the Midland reduction being a seminal example. Here, a turnover strategy for asymmetric catalysis, boron.oxygen transb

Synthesis of Alkylidene(gem-Difluorocyclopropanes) from Propargyl Glycolates by a One-Pot Difluorocyclopropenation/Ireland-Claisen Rearrangement Sequence

A one-pot difluorocyclopropenation/Ireland-Claisen rearrangement sequence applied to readily available propargyl glycolates was developed as a route toward functionalized alkylidene(gem-difluorocyclopropanes). This strategy conveniently avoids the isolation of the unstable 3,3-difluorocyclopropenylcarbinyl glycolates arising from the difluorocyclopropenation. The Ireland-Claisen rearrangement proceeds with high diastereoselectivity and chirality transfer to afford alkylidene(gem-difluorocyclopropanes) incorporating a quaternary stereocenter and a protected glycolic acid moiety, which are useful building blocks for the preparation of functionalized gem-difluorocyclopropanes.

Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of Propargylic Ketones

The asymmetric transfer hydrogenation of α,β-propargyl ketones catalyzed by an in situ formed ruthenium-hydroxyamide complex was explored. The acetylenic alcohols were isolated in good to excellent yields with excellent ee values (typically >90 %) after s

Asymmetric hydrogenation of alkynyl ketones with the η6- arene/TsDPEN-ruthenium(II) catalyst

Enantioselective hydrogenation of alkynyl ketones catalyzed by Ru(OTf)(TsDPEN)(η6-p-cymene) (TsDPEN = N-(p-toluenesulfonyl)-1,2- diphenylethylenediamine) affords the propargylic alcohols in up to 97% ee. The alkynyl moieties are left intact in most cases. The reaction can be conducted with a substrate-to-catalyst molar ratio as high as 5000 under 10 atm of H 2. The mode of enantioselection is elucidated with the transition state models directed by the CH/π attractive interaction between the substrate and the catalytic species.

Unambiguous determination of the absolute configurations of acetylene alcohols by combination of the Sonogashira reaction and the CD exciton chirality method - Exciton coupling between phenylacetylene and benzoate chromophores

The CD exciton chirality method was applied to various phenylacetylene alcohols to determine their absolute configurations; the long axis polarized π-π* transition (λmax = 252 nm) of the 4-methoxyphenylacetylene chromophore couples with the tra

Enantioselective synthesis of both enantiomers of various propargylic alcohols by use of two oxidoreductases

The oxidoreductases Lactobacillus brevis alcohol dehydrogenase (LBADH) and Candida parapsilosis carbonyl reductase (CPCR) are suitable catalysts for the reduction of ketones to afford enantiopure sec. alcohols. A broad variety of alkynones (1, 3, and 5) are accepted as substrates and the corresponding propargylic alcohols (2, 4, and 6) are obtained in good yield and excellent enantiomeric excess. By changing the steric demand of the substituents the ee values can be adjusted and even the configurations of the products can be altered.

Lipase-catalyzed kinetic resolution of 3-butyn-2-ol

Optically active 3-butyn-2-ol, an important building block, was synthesized successfully using lipase-catalyzed kinetic resolution. Starting from the thus obtained 3-butyn-2-ol, several 4-aryl-substituted compounds were synthesized enantioselectively.