112459-63-9Relevant academic research and scientific papers
Stereocontrolled Diels-Alder Reactions with Chiral Tricyclic Oxazolidinones
Tanaka, Kazuhiko,Uno, Hiroe,Osuga, Hideji,Suzuki, Hitomi
, p. 629 - 632 (1993)
(1R,2R,6S,7S)-5-Aza-1,10,10-trimethyl-3-oxatricyclo2,6>decan-4-one (endo-oxazolidinone) and (1R,2R,6R,7S)-isomer (exo-oxazolidinone) are found to be efficient diastereomeric auxiliaries for Diels-Alder reactions, which are promoted by L
Scalable and Highly Diastereo- and Enantioselective Catalytic Diels-Alder Reaction of α,β-Unsaturated Methyl Esters
Gatzenmeier, Tim,Turberg, Mathias,Yepes, Diana,Xie, Youwei,Neese, Frank,Bistoni, Giovanni,List, Benjamin
supporting information, p. 12671 - 12676 (2018/10/15)
Despite tremendous advances in enantioselective catalysis of the Diels-Alder reaction, the use of simple α,β-unsaturated esters, one of the most abundant and useful class of dienophiles, is still severely limited in scope due to their low reactivity. We report here a catalytic asymmetric Diels-Alder methodology for a large variety of α,β-unsaturated methyl esters and different dienes based on extremely reactive silylium imidodiphosphorimidate (IDPi) Lewis acids. Mechanistic insights from accurate domain-based local pair natural orbital coupled-cluster (DLPNO-CCSD(T)) calculations rationalize the catalyst control and stereochemical outcome.
SYNTHESIS OF ENANTIOMERICALLY PURE (5S)-4-AZA-2-OXA-6,6-DIMETHYL-7,10-METHYLENE-5-SPIRODECAN-3-ONE, A NOVEL CHIRAL OXAZOLIDIN-2-ONE FROM (-)-CAMPHENE FOR USE AS A RECYCLABLE CHIRAL AUXILIARY IN ASYMMETRIC TRANSFORMATIONS
Banks, Malcolm R.,Cadogan, J. I. G.,Gosney, Ian,Grant, Keith J.,Hodgson, Philip K. G.,Thorburn, Paul
, p. 199 - 206 (2007/10/02)
By an intramolecular nitreno-mediated route (-)-camphene is transformed into a novel spiro-oxazolidin-2-one whose efficiency as a chiral auxiliary is highlighted by the excellent levels of chiral induction attained in an array of asymmetric transformations such as the Diels-Alder, conjugate addition, aldol condensation, alkylation and acylation reactions.
