80098-80-2

Upstream product

• 64269-40-5 2,4-dimethyl-4-phenyl-1,3-dioxane 
• 1200-73-3 4-methyl-4-phenyl-1,3-dioxane 
• 75-07-0 acetaldehyde 
• 50-00-0 formaldehyd 
• 98-83-9 isopropenylbenzene 
• 70588-46-4 (Z)-penta-1,3-dien-2-ylbenzene 

Downstream Products

• 1391824-23-9 (E)-3-phenylhex-3-en-1-ol 

Relevant academic research and scientific papers

A Structurally Robust Chiral Borate Ion: Molecular Design, Synthesis, and Asymmetric Catalysis

Catalysis by chiral weakly-coordinating anions (WCAs) remains underdeveloped due to the lack of a molecular design strategy for exploiting their characteristics, such as the non-nucleophilic nature. Here, we report the development of a chiral borate ion comprising an O,N,N,O-tetradentate backbone, which ensures hitherto unattainable structural robustness. Upon pairing with a proton, the hydrogen borate acts as an effective catalyst for the asymmetric Prins-type cyclization of vinyl ethers, providing access to structurally and stereochemically defined dihydropyrans. The key to selectivity control is the distinct ability of the borate ion to discriminate the prochiral faces of the acyclic oxonium ion intermediate and dictate the regiochemical outcome. We anticipate that this study paves the way for exploring the untapped potential of WCA catalysis for selective chemical synthesis.

Catalytic ring expansion of vinyl oxetanes: Asymmetric synthesis of dihydropyrans using chiral counterion catalysis

Acid Showdown! The first catalytic ring expansion of vinyl oxetanes to 3,6-dihydro-2H-pyrans is described. Copper(II) triflate emerged as the best catalyst for this new transformation, which has broad scope as demonstrated by the eighteen examples included. The symmetric vinyl oxetane substrate can be asymmetrically desymmetrized when using either chiral Lewis or Bronsted acids as catalysts. Copyright

Cationic iron(III) porphyrin-catalyzed [4 + 2] cycloaddition of unactivated aldehydes with simple dienes

Cationic iron(III) porphyrin was found to be an efficient catalyst for the highly chemoselective hetero-Diels-Alder-type reaction of aldehydes with 1,3-dienes. The catalyzed process did not require the use of electron-deficient aldehydes such as glyoxylic acid derivatives or activated electron-rich 1,3-dienes such as Danishefsky's diene and Rawal's diene. The high functional group tolerance and robustness of the catalyst were demonstrated. Further, the potential utility of the catalyst was demonstrated by performing the cycloaddition in the presence of water and by carrying out cycloaddition of an unactivated ketone such as cyclohexanone with a diene.

SYNTHESIS OF SUBSTITUTED 5,6- AND 3,6-DIHYDRO-2H-PYRANS BY ACID CONDENSATION OF ISOBUTYLENE AND α-METHYLSTYRENE WITH ALIPHATIC ALDEHYDES

2,4-Disubstituted dihydropyrans, isomeric with respect to the position of the double bond, were obtained by the reaction of isobutylene and α-methylstyrene with formaldehyde and aliphatic aldehydes.

PRODUCTION OF SUBSTITUTED 5,6- AND 3,6-DIHYDRO-2H-PYRANS FROM 4,4-DIMETHYL- AND 4-METHYL-4-PHENYL-1,3-DIOXANES AND CARBONYL COMPOUNDS

2,4-Disubstituted and 2,2,4-trisubstituted dihydropyrans, isomeric with respect to the position of the double bond, were obtained by the reaction of 4,4-dimethyl- and 4-methyl-4-phenyl-1,3-dioxanes with aldehydes and ketones.The effects of temperature and of the amount and nature of the catalyst on the direction and selectivity of the reaction were investigated.