28968-34-5

Upstream product

• 16141-26-7 ethyl 3-hydroxy-2-methyl-2-phenylpropanoate 
• 24765-53-5 2-methyl-2-phenylpropane-1,3-diol 
• 1124258-92-9 C₁₀H₁₂O₂ 
• 34713-70-7 2-Phenylpropanal 
• 1369965-81-0 2-((R)-1-(benzyloxy)-2-phenylpropan-2-yl)benzo-1,3-dithiole 
• 1369965-69-4 C₁₆H₁₆OS₂ 

Downstream Products

• 105498-87-1 (+)-2-(diethylamino)ethyl 2-methyl-2-phenyl-3-(tosyloxy)propanoate 
• 99553-27-2 (+)-2-(diethylamino)ethyl α-methyltropate 

Relevant academic research and scientific papers

Enantioselective Desymmetrization of 1,3-Diols by a Chiral DMAP Derivative

We developed an enantioselective desymmetrization of 1,3-diols by a chiral N,N-dimethyl-4-aminopyridine (DMAP) derivative containing a 1,1-binaphthyl with tert-alcohol units. The reactions required only 0.1 mol% of catalyst and showed moderate to high chemoselectivity (monoacylation vs. diacylation) and enantioselectivity (14 examples, up to 95:5 er). Several control experiments revealed that diol units in both the substrate and the catalyst are important to achieve high enantioselectivity.

Enantioselective Synthesis of Functionalized Quaternary Stereocenters

An enantioselective synthesis of functionalized quaternary stereocenters was developed from amino alcohol derived (bromoalkylidene)morpholinones. Stereoselective cross-coupling of the morpholinones with arylboronic acids or alkyl trifluoroborates provided a variety of disubstituted alkylidenemorpholinones. A highly stereoselective Prins reaction of the cross-coupling products generated the target quaternary stereocenter. The Prins products are readily converted into a variety of acyclic, enantiomerically enriched, functionalized building blocks with a quaternary stereocenter.

Chiral phosphoric acid catalyzed highly enantioselective desymmetrization of 2-substituted and 2,2-disubstituted 1,3-diols via oxidative cleavage of benzylidene acetals

A highly enantioselective catalytic protocol for the desymmetrization of a wide variety of 2-substituted and 2,2-disubstituted 1,3-diols is reported. This reaction proceeds through the formation of an "ortho ester" intermediate via oxidation of 1,3-diol benzylidene acetal by dimethyldioxirane (DMDO) and the subsequent proton transfer catalyzed by chiral phosphoric acid (CPA). The mechanism and origins of enantioselectivity of this reaction are identified using DFT calculations. The oxidation by DMDO is rate-determining, and the phosphoric acid significantly accelerates the proton transfer; the attractive interactions between the benzylidene part of the substrate and the 2,4,6-triisopropyl group of CPA are the key to high enantioselectivity.

A general stereoselective enamine mediated alkylation of α-substituted aldehydes

We herein present a general enamine-mediated α-alkylation of α-substituted aldehydes with carbenium ions for the stereoselective construction of quaternary stereogenic centers.

Molecular Modification of Anticholinergics as Probes for Muscarinic Receptors. 2. Amino Esters of α-Methyltropic Acid

As a continuation of our goals to study molecular probes for muscarinic cholinergic receptors, a series of 3-substituted 2-methyl-2-phenylpropanoates with the general structure C6H5C(CH2X)CH3)COOCH2CH2NEt2 where X=OH, OTs, F, Cl, Br, I, and OAc were prepa