354150-89-3Relevant academic research and scientific papers
Reversal of enantioselectivity induced by the achiral part of an organocatalyst in a Diels-Alder reaction
Tawde, Trupti S.,Wagh, Swapnil J.,Sapre, Jai V.,Khose, Vaibhav N.,Badani, Purav M.,Karnik, Anil V.
, p. 130 - 135 (2016)
A new series of chiral organocatalysts was developed by attaching achiral heterocyclic units via a methylene group to (S)-2-hydroxyethylbenzimidazole for the asymmetric Diels-Alder reaction between anthrone enolate and maleimides. While organocatalysts wi
Chiral primary amino alcohol organobase catalysts for the asymmetric Diels-Alder reactions of anthrones with maleimides
Kumagai, Jun,Otsuki, Teppei,Subba Reddy,Kohari, Yoshihito,Seki, Chigusa,Uwai, Koji,Okuyama, Yuko,Kwon, Eunsang,Tokiwa, Michio,Takeshita, Mitsuhiro,Nakano, Hiroto
, p. 1423 - 1429 (2015/12/09)
Simple chiral triethylsilyl-amino alcohol organocatalysts containing a bulky triethylsilyl group on the oxygen atom at the γ-position were designed and synthesized as new organocatalysts for enantioselective Diels-Alder reactions of anthrones with maleimides to produce chiral hydroanthracene Diels-Alder adducts in up to 99% yield and with up to 94% ee.
Enantioselective Diels-Alder reaction of anthrone and maleimide catalyzed by a simple chiral tertiary amine
Bai, Jian-Fei,Guo, Yun-Long,Peng, Lin,Jia, Li-Na,Xu, Xiao-Ying,Wang, Li-Xin
, p. 1229 - 1233 (2013/02/23)
Simple chiral tertiary amines with a special imide skeleton were first successfully applied to catalyze the enantioselective D-A reaction of anthrone and maleimides in excellent yields (up to 96%) and enantioselectivities (up to 95% ee).
Asymmetric organocatalytic anthrone additions to activated alkenes
Zea, Alex,Alba, Andrea-Nekane R.,Bravo, Natalia,Moyano, Albert,Rios, Ramon
experimental part, p. 2513 - 2529 (2011/04/24)
Asymmetric organocatalytic additions of anthrones to activated alkenes are discussed. The reaction between anthrone or dithranol and α,β- unsaturated aldehydes is catalyzed by diphenylprolinol trimethylsilyl ether in toluene at -40 °C, giving the Michael
A first case of asymmetric catalysis induced by metal-free bisoxazolines
Akalay, Deniz,Duerner, Gerd,Goebel, Michael W.
supporting information; experimental part, p. 2365 - 2368 (2009/04/05)
Metal-free bisoxazolines catalyze the Diels-Alder reaction of N-substituted maleimides with anthrone derivatives leading to products in excellent yields and enantioselectivities up to 70%. A mechanism relying on Bronsted-base catalysis is assumed to be involved with formation of an ion pair between the protonated catalyst and the anthrone enolate, which acts as a diene. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
