80098-80-2Relevant articles and documents
A Structurally Robust Chiral Borate Ion: Molecular Design, Synthesis, and Asymmetric Catalysis
Kizu, Tomohito,Ooi, Takashi,Takahashi, Wakana,Tanaka, Naoya,Ueoka, Fumito,Uraguchi, Daisuke
, p. 11456 - 11461 (2020)
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.
Cationic iron(III) porphyrin-catalyzed [4 + 2] cycloaddition of unactivated aldehydes with simple dienes
Fujiwara, Kyohei,Kurahashi, Takuya,Matsubara, Seijiro
supporting information; experimental part, p. 5512 - 5515 (2012/05/20)
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.
DEHYDRATION OF 2- AND 2,2-SUBSTITUED 4,4-DIMETHYL- AND 4-METHYL-4-PHENYL-1,3-DIOXANES
Romanov, N. A.,Kantor, E. A.,Musavirov, R. S.,Karakhanov, R. A.,Rakhmankulov, D. L.
, p. 140 - 143 (2007/10/02)
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