569656-50-4Relevant academic research and scientific papers
Kinetic Enzymatic Resolution of Cyclopropane Derivatives
Pietruszka, Joerg,Rieche, Anja C. M.,Wilhelm, Thorsten,Witt, Andreas
, p. 1273 - 1286 (2007/10/03)
The kinetic enzymatic resolution of various cyclopropane derivatives was systematically investigated. The study focused on synthetically useful cyclopropylmethanols (e.g., 18a/j or 19a/j) as well as some rarely investigated cyclopropanols (e.g., 24/25 or 27). The combination of enantioselective catalytic or diastereoselective synthesis of enantiomerically enriched compounds with enzymatic approaches ultimately led to the most convenient route to enantiomerically pure starting materials. Again, this was especially proven for the synthesis of cyclopropanols 18a/j and 19a/j. Key to the successful investigation was to rigorously establish an analytical tool for the analysis of enantiomeric composition of reaction mixtures.
Synthesis of spirocycles via ring closing metathesis of heterocycles carrying gem-diallyl substituents obtained via ring opening of (halomethyl)cyclopropanes with allyltributyltin
Gurjar, Mukund K.,Ravindranadh, Somu V.,Sankar, Kuppusamy,Karmakar, Sukhen,Cherian, Joseph,Chorghade, Mukund S.
, p. 1366 - 1373 (2007/10/03)
In the presence of allyl tri-n-butyltin-AlBN, cyclopropylmethyl bromides/xanthates undergo ring-opening reaction with concomitant formation of geminal diallyl derivatives in good yields. The ring closing metathesis reactions on geminal diallyl derivatives with Grubbs' catalyst provided spirocyclopentenyl products. Combination of these two methodologies has been applied to the synthesis of mono-, bis-cyclopentyl-carbohydrates as well as spirocyclopentylproline derivatives.
