371153-91-2

Upstream product

• 74181-34-3 2,2,-dimethyl-1,3-dioxan-5-one 
• 108-91-8 cyclohexylamine 

Downstream Products

• 221887-91-8 4-(but-3-enyl)-2,2-dimethyl-1,3-dioxan-5-one 
• 1072451-67-2 4-benzyl-2,2-dimethyl-1,3-dioxan-5-one 
• 1072451-10-5 (S)-2,2,4-trimethyl-4-(2-phenylallyl)-1,3-dioxan-5-one 

Relevant academic research and scientific papers

Formal synthesis of englerin A utilizing regio- and diastereoselective [4+3] cycloaddition

Englerin A, a guaiane sesquiterpene isolated from Phyllanthus engleri, showed highly potent and selective growth inhibitory activities against renal cancer cell lines. We synthesized the key tricyclic intermediate from commercially available 2,2-dimethyl-1,3-dioxan-5-one via regio- and diastereoselective [4+3] cycloaddition between the formyl enol silyl ether and the disubstituted furan, in 4.8% total yield over 10 steps.

Enantioselective decarboxylative alkylation reactions: Catalyst development, substrate scope, and mechanistic studies

α-Quaternary ketones are accessed through novel enantioselective alkylations of allyl and propargyl electrophiles by unstabilized prochiral enolate nucleophiles in the presence of palladium complexes with various phosphinooxazoline (PHOX) ligands. Excellent yields and high enantiomeric excesses are obtained from three classes of enolate precursor: enol carbonates, enol silanes, and racemic β-ketoesters. Each of these substrate classes functions with nearly identical efficiency in terms of yield and enantioselectivity. Catalyst discovery and development, the optimization of reaction conditions, the exploration of reaction scope, and applications in target-directed synthesis are reported. Experimental observations suggest that these alkylation reactions occur through an unusual inner-sphere mechanism involving binding of the prochiral enolate nucleophile directly to the palladium center. Sly as a PHOX: The development of an enantioselective decarboxylative palladium-catalyzed allylic alkylation reaction, utilizing phosphinooxazoline ligands, is described. The catalyst is applied to a range of allyl enol carbonate, silyl enol ether, and allyl β-ketoester substrates to provide alkylated ketone products in excellent yield and good ee (see scheme). The utility of these products is demonstrated by their use in several asymmetric syntheses. Mechanistic studies are reported suggesting an unusual inner-sphere mechanism. Copyright

A facile construction of Bi-or tricyclic skeletons by nickel-catalyzed stereoselective cyclization of alkynylcycloalkanone

(Equation Presented). A nickel-catalyzed intramolecular cyclization of alkynylalkanone in the presence of Et3SiH using an NHC ligand produced various carbo-and heterocycles in a stereoselective manner. The reaction would proceed via formation o

Catalytic enantioselective alkylation of substituted dioxanone enol ethers: ready access to C(α)-tetrasubstituted hydroxyketones, acids,and esters

(Chemical Equation Presented) Adaptive Alkylation: Palladium-catalyzed asymmetric alkylation enables access to fully substituted enantioenriched oxygenated stereocenters, which can be transformed easily to α-hydroxyketones, esters, and acids, providing a catalytic, enantioselective synthesis for natural products.

Stereoselective preparation of (Z)-2-(trialkylsilyloxy)-2-alkenals by retrocycloaddition reactions of 4H-4-alkyl-5-(trialkylsilyloxy)-1,3-dioxins. Useful reactants for Lewis acid catalyzed [4 + 3] cyclizations

(matrix presented) Retrocycloadditions of 4H-4-alkyl-5-(trialkylsilyloxy)-1,3-dioxins proceed smoothly in refluxing toluene to afford (Z)-2-(trialkylsilyloxy)-2-alkenals with complete stereoselectivity. These enals undergo Sasaki-type [4 + 3] cyclizations