176484-48-3Relevant academic research and scientific papers
First intramolecular enantioselective iridium-catalysed allylic animations
Welter, Carolin,Koch, Oliver,Lipowsky, Gunter,Helmchen, Guenter
, p. 896 - 897 (2004)
Enantioselective indium-catalysed intramolecular allylic aminations, using phosphinooxazolines or phosphorus amidites as ligands, provided ee values of >90%, at a catalyst loading of a marked preference for intra- over corresponding intermolecular reactions.
Enantioselective synthesis of N-heterocycles via intramolecular Pd(0)-catalysed allylic amination
Olszewska, Beata,Kryczka, Bogus?aw,Zawisza, Anna
, p. 9551 - 9556 (2013/10/22)
An efficient and stereoselective synthesis of pyrrolidine-, piperidine-, and azepane-type N-heterocycles is described by the intramolecular Pd(0)-catalysed cyclisation of amino allylic carbonates. The use of chiral ligands gave the corresponding heterocyclic derivatives having er values that were from moderate to good.
Synthesis of the bicyclic core of pumiliotoxins
Sudau, Alexander,Muench, Winfried,Bats, Jan-W.,Nubbemeyer, Udo
, p. 3304 - 3314 (2007/10/03)
The bicyclic core of the pumiliotoxins was synthesized in nine to eleven steps starting from L-(-)-proline. This chiral pool starting material was initially converted into an optically active 2-vinylpyrrolidine by standard operations. The first key step allowed the generation of a nine-membered ring lactam by means of a zwitterionic aza-Claisen rearrangement. The 1,4 chirality transfer was found to be low, but the double bond of the azoninone was generated with an exclusive trans configuration in a planar-S arrangement. The mixture of diastereomers thus obtained was immediately epoxidized; the planar chiral information could be completely used to build up new stereogenic centers. Subsequent ring closure under hydrogenolytic conditions resulted in the formation of the bicyclic core with a bridgehead of defined configuration. The hydroxyl group of that material could be protected as a TBS ether, or alternatively a sequence of a Swern oxidation and subsequent methyl Grignard addition gave the complete bicyclic framework with low C8 diastereoselectivity. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Photochemical reaction between tertiary allylic amines and chromium carbene complexes: Synthesis of lactams via a zwitterion aza cope rearrangement
Deur, Christopher J.,Miller, Michael W.,Hegedus, Louis S.
, p. 2871 - 2876 (2007/10/03)
Photolysis of chromium carbene complexes in the presence of tertiary allylic amines resulted in a zwitterionic aza Cope rearrangement to produce unsaturated lactams in fair yield.
