871682-78-9

Upstream product

• 65738-56-9 methyl 5-chloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate 
• 75-65-0 tert-butyl alcohol 

Downstream Products

• 1041024-81-0 (S)-tert-butyl 5-chloro-1-oxo-2-(2-(2-(trifluoromethyl)phenylsulfonamido)ethyl)-2,3-dihydro-1H-indene-2-carboxylate 
• 1620093-33-5 C₂₄H₁₅ClO₃Se 
• 1443150-77-3 C₂₀H₁₉ClO₃S 
• 1264375-42-9 (R)-tert-butyl 2-benzyl-5-chloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate 
• 1078713-93-5 (S)-tert-butyl 5-chloro-2-(2-(4-methylphenylsulfonamido)ethyl)-1-oxo-2,3-dihydro-1H-indene-2-carboxylate 

Relevant academic research and scientific papers

Ring-Strain-Enabled Catalytic Asymmetric Umpolung C-O Bond-Forming Reactions of 1,2-Oxazetidines for the Synthesis of Functionalized Chiral Ethers

An unprecedented catalytic asymmetric umpolung C-O bond-forming reaction of N-nosyl 1,2-oxazetidines with β-keto esters has been achieved in the presence of a chiral phase-transfer catalyst, allowing access to a range of highly functionalized chiral ethers bearing quaternary and no adjacent stereogenic centers with high yields, excellent enantioselectivities, and diastereoselectivities (up to 97percent ee and 20:1 dr). These versatile products could be flexibly transformed into biologically important chiral fused and spiro morpholines in two steps.

Chiral N,N'-Dioxide Organocatalyzed Asymmetric Electrophilic α-Cyanation of β-Keto Esters and β-Keto Amides

An enantioselective electrophilic α-cyanation of 1-indanone-derived β-keto esters and β-keto amides using a hypervalent iodine as the cyanide-transfer reagent was realized. A chiral N,N'-dioxide was used as the efficient bifunctional organocatalyst in the presence of inorganic base, which gave the corresponding α-cyano dicarbonyl compounds in yields of 50-99% with good enantioselectivities (87-97% ee).

Photo-organocatalytic enantioselective perfluoroalkylation of β-ketoesters

The visible-light-driven, phase-transfer-catalyzed, enantioselective perfluoroalkylation and trifluoromethylation of cyclic β-ketoesters is described. The photo-organocatalytic process, which occurs at ambient temperature and under visible light illumination, is triggered by the photochemical activity of in situ-generated electron donor-acceptor complexes, arising from the association of chiral enolates and perfluoroalkyl iodides. Preliminary mechanistic studies are reported.

Catalytic asymmetric cross-dehydrogenative coupling: Activation of C-H bonds by a cooperative bimetallic catalyst system

A cooperative bimetallic catalyst system was applied in the catalytic asymmetric cross-dehydrogenative coupling of β-ketoesters and xanthene. Various optically active xanthene derivatives bearing a quaternary stereogenic carbon center were obtained in moderate to good yields (up to 90%) with excellent enantioselectivities (up to 99% ee). Meanwhile, a transition-state model was proposed to explain the origin of the asymmetric induction.

Organocatalytic asymmetric conjugate addition to allenic esters and ketones

The first example of an organocatalytic enantioselective conjugate addition of cyclic β-ketoesters and glycine imine derivatives to electron-deficient allenes is described. We disclose that the corresponding chiral β,γ-unsaturated carbonyl compounds are formed exclusively under phase-transfer conditions using either cinchona-alkaloid-derived or biphenyl-based chiral quaternary ammonium salts as catalysts. The scope of the reaction for β-ketoesters is outlined for allenes having a ketone or ester motif as electron-withdrawing group as well as different substituents in the 3-position, giving the optically active products in high yields and excellent diastereo- and enantioselectivities (90-96% ee). The conjugate addition also proceeds for a number of cyclic β-ketoesters having different ring sizes, ring systems, and substituents in high yields and enantioselectivities. Glycine imine derivatives also undergo the asymmetric conjugate addition to electron-deficient allenes in high yields and with enantioselectivities in the range of 60-88% ee, thus providing a rapid entry to optically active α-vinyl-substituted α-amino acid derivatives. It is shown that the enantioselectivity is strongly dependent on the size of the ester moiety of the nucleophile in combination with the catalytic system used. The high synthetic value of the chiral products arising from these new catalytic processes is demonstrated by two straightforward transformations leading in one case to optically active hexahydrobenzopyranones and in the other to substituted pyroglutamates (γ-lactames).

Organocatalytic asymmetric "anti-Michael" reaction of β-ketoesters

The first organocatalytic "anti-Michael" reaction of cyclic-β-ketoesters to unsaturated double bonds is described in a highly asymmetric version leading to the synthesis of α,α′- disubstituted branched double bonds as optically active Baylis-Hillman-like adducts. The Royal Society of Chemistry.

Construction of quaternary stereocenters by efficient and practical conjugate additions to α,β-unsaturated ketones with a chiral organic catalyst

(Chemical Equation Presented) Added value: The conjugate addition of cyclic or acyclic α-substituted β-ketoesters to α,β-unsaturated ketones using a chiral organic catalyst (1) can be achieved with good enantioselectivity, diastereoselectivity, and yield. This asymmetric C-C bond formation strategy provides a range of chiral building blocks 2 that contain an all-carbon quaternary stereocenter.

ASYMMETRIC MICHAEL AND ALDOL ADDITION USING BIFUNCTIONAL CINCHONA-ALKALOID-BASED CATALYSTS

One aspect of the present invention relates to quinine-based and quinidine-based catalysts. Another aspect of the invention relates to a method of preparing a derivatized quinine-based or quinidine-based catalyst comprising 1) reacting quinine or quinidine with 5 base and a compound that has a suitable leaving group, and 2) converting the ring methoxy group to a hydroxy group. Another aspect of the present invention relates to a method of preparing a chiral, non-racemic compound from a prochiral electron-deficient alkene or azo compound or prochiral aldehyde or prochiral ketone, comprising the step of: reacting a prochiral electron-deficient alkene or azo compound or prochiral aldehyde or prochiral 10 ketone with a nucleophile in the presence of a catalyst; thereby producing a chiral, non racemic compound; wherein said catalyst is a derivatized quinine or quinidine. Another aspect of the present invention relates to a method of kinetic resolution, comprising the step of reacting racemic chiral alkene with a nucleophile in the presence of a derivatized quinine or quinidine.