165072-41-3

Upstream product

• 124688-07-9 6-methoxy-2,2-dimethyl-1-indanone 
• 13623-25-1 6-methoxy-2,3-dihydro-1H-inden-1-one 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

Scalable Synthesis of a Chiral Selenium π-Acid Catalyst and Its Use in Enantioselective Iminolactonization of β,γ-Unsaturated Amides

Chiral selenium π-acid catalysis has for a long time been lagging behind other areas of asymmetric catalysis due to a lack of highly enantioselective catalysts. In this regard, we recently developed the first chiral selenium π-acid catalyst which performs the oxidative cyclization of β,γ-unsaturated carboxylic acids with high enantioselectivities. We report herein our improved synthesis of this chiral selenium catalyst, which allows access to a large quantity of the catalyst as the diselenide. In addition, the catalyst is tested in the oxidative cyclization of N -methoxy β,γ-unsaturated amides to give iminolactones with high enantioselectivities.

Silylative Kinetic Resolution of Racemic 2,2-Dialkyl 5- and 6-Membered Cyclic Benzylic Alcohol Derivatives Catalyzed by Chiral Guanidine, (R)-N-Methylbenzoguanidine

Efficient silylative kinetic resolution of racemic 2,2-dialkyl 5- and 6-membered cyclic benzylic alcohols was achieved using diphenylmethylchlorosilane (Ph2MeSiCl) or phenyldimethylchlorosilane (PhMe2SiCl) as a silyl source catalyzed by chiral guanidine. The reaction could be applied to a broad range of 2,2-dialkyl 1-indanols with good s-values, irrespective of the electronic nature of the substituent on the aromatic ring of the substrates and the type of substituent at the C2-position. In addition, several 2,2-dimethyl 6-membered cyclic and heterocyclic alcohols could be adopted in the reaction. (Figure presented.).

A Chiral Electrophilic Selenium Catalyst for Highly Enantioselective Oxidative Cyclization

Chiral electrophilic selenium catalysts have been applied to catalytic asymmetric transformations of alkenes over the past two decades. However, highly enantioselective reactions with a broad substrate scope have not yet been developed. We report the first successful example of this reaction employing a catalyst based on a rigid indanol scaffold, which can be easily synthesized from a commercially available indanone. The reaction efficiently converts β,γ-unsaturated carboxylic acids into various enantioenriched γ-butenolides under mild conditions.

The Photochemistry of Conformationally Rigid Benzylic Esters: 2,2-Dimethyl-1-indanyl Acetates and Pivalates

The photochemistry, in methanol, of substituted 2,2-dimethyl-1-indanyl acetates 9a-c and pivalates 10a-c has been studied.In agreement with previous studies on benzylic esters, the results show that the substituents change the yield of products derived from the ion pair.The mechanistic conclusion reached is that the substituents change the oxidation potential of the indanyl radicals and thus the rate constant of electron transfer for converting the radical pair to the ion pair.The results also reveal two other substituent effects.First, substituents can increase the overall efficiency of the photoreaction by enhancing homolytic cleavage.The second effect is conformational.In compounds where the bond that is cleaving is conformationally mobile, such as the C-O bond in benzylic esters, substituents on the ring can change the population of the reactive conformer and thus the overall efficiency of the reaction.For the indanyl acetate esters, the difference in excited-state reaction rate between the m- and p-methoxy substituted ester is 15:1.For the m- and p-methoxy substituted benzyl acetates, this difference in reaction rate is 48:1.The larger difference in reaction rate for the conformationally mobile benzylic esters is attributed to a higher population of the unreactive conformer for the p-methoxy substituted ester.