67260-13-3

Upstream product

• 1914-65-4 tetralin-1-carboxylic acid 

Downstream Products

• 1914-65-4 tetralin-1-carboxylic acid 
• 1352790-95-4 (S)-2,2-dimethyl-3-((2,4,6-triisopropylphenyl)sulfonyl)-1,3-oxazolidine-4-carbaldehyde 
• 1377824-29-7 (S)-3',4'-dihydro-2'H-spiro[indoline-3,1'-naphthalen]-2-one 

Relevant academic research and scientific papers

Origins of diastereoselectivity in lewis acid promoted ketene-alkene [2 + 2] cycloadditions

A detailed analysis of a Lewis acid promoted ketene-alkene [2 + 2] cycloaddition is reported. The studies have led to a rationalization for an observed inversion of diastereoselectivity between thermally induced and Lewis acid promoted ketene-alkene [2 + 2] cycloadditions. The model is supported with both experimental and computational results.

Forming All-Carbon Quaternary Stereocenters by Organocatalytic Aminomethylation: Concise Access to β2,2-Amino Acids

The asymmetric synthesis of β2,2-amino acids remains a formidable challenge in organic synthesis. Here a novel organocatalytic enantioselective aminomethylation of ketenes with stable and readily available N,O-acetals is reported, providing β2,2-amino esters bearing an all-carbon quaternary stereogenic center in high enantiomeric ratios with a catalytic amount of chiral phosphoric acid. Typically, this transformation probably proceeds through an asymmetric counter-anion-directed catalysis. As a result, a concise, practical, and atom-economic protocol toward rapidly access to β2,2-amino acids has been developed.

Lewis acid-promoted ketene-alkene [2 + 2] cycloadditions

Described are the first examples of ketene-alkene [2 + 2] cycloadditions promoted by Lewis acids. Notable features of this method include (1) substantial rate acceleration relative to traditional thermal reactions, (2) good diastereoselectivities and yields for the formation of the cyclobutanone products, and (3) inverse diastereoselectivity compared with related thermal cycloadditions for many examples. These studies not only provide access to synthetically versatile cyclobutanones that cannot be prepared by traditional thermal cycloadditions but also address important mechanistic questions regarding ketene-alkene [2 + 2] cycloaddition reactions.