1029539-77-2Relevant academic research and scientific papers
Gold(I)-catalysed cycloisomerisation of 1,6-cyclopropene-enes
Miege, Frederic,Meyer, Christophe,Cossy, Janine
supporting information; experimental part, p. 7810 - 7822 (2012/08/07)
The gold(I)-catalysed cycloisomerisation of appropriately substituted 1,6-cyclopropene-enes proceeds through regioselective electrophilic ring opening of the three-membered ring to generate an alkenyl gold carbenoid that achieves the intramolecular cyclopropanation of the remote olefin. This strategy allows straightforward, highly efficient and diastereoselective access to a variety of substituted 3-oxaand 3-azabicycloachtungtrenung[4.1.0]heptanes, as well as to bicycloachtungtrenung[4.1.0]heptan-3-ol derivatives. Since the isopropylidene group in the resulting cycloisomerisation products can be subjected to ozonolysis, 3,3-dimethylcyclopropenes behave as interesting surrogates for a-diazoketones.
Diastereoselective access to trans -2-substituted cyclopentylamines
Joosten, Antoine,Lambert, Emilie,Vasse, Jean-Luc,Szymoniak, Jan
supporting information; experimental part, p. 5128 - 5131 (2011/01/05)
A highly diastereoselective synthesis of trans-2-substituted cyclopentylamines via a tandem hydrozirconation/Lewis acid-mediated cyclization sequence applied to butenyl oxazolidines is described. The method allows an easy preparation of diversely substituted cyclopentylamines which appear to be useful synthetic intermediates. This was further illustrated by the syntheses of (±)-Rodocaine, (±)-trans-pentacin, and enantiomerically enriched trans-cyclopentane-1,2-diamine.
Directed diastereoselectivity in the asymmetric Claisen/metathesis reaction sequence
Probst, Nicolas P.,Haudrechy, Arnaud,Ple, Karen
, p. 4338 - 4341 (2008/09/21)
(Chemical Equation Presented) The Claisen/metathesis sequence is a versatile synthetic tool for the synthesis of quaternary hydroxy and amino acid carbocycles. By correctly choosing both the configuration of the allylic alcohol and the double bond geometry, specific access to any one of four possible stereoisomers is possible in good yield and excellent diastereoselectivity. The enantiomerically pure allylic alcohols are easily obtained by addition of terminal alkynes to aldehydes. Controlled reduction of the triple bond then gives the desired double bond geometry.
