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Palladium-Catalyzed Enantioselective Decarboxylative Cycloaddition of Vinylethylene Carbonates with Isocyanates
Ist Teil von
Chemistry : a European journal, 2015-01, Vol.21 (1), p.120-124
Ort / Verlag
Weinheim: WILEY-VCH Verlag
Erscheinungsjahr
2015
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
An efficient method for the enantioselective construction of β‐substituted β‐vinylglycinol derivatives through palladium‐catalyzed decarboxylative cycloaddition of vinylethylene carbonates with isocyanates was developed. By using a palladium complex generated in situ from [Pd2(dba)3]⋅CHCl3 (dba=dibenzylideneacetone) and (S)‐Segphos as a catalyst under mild reaction conditions, the process provided 4‐substituted‐4‐vinyloxazolidin‐2‐ones in high yields with a high level of enantioselectivity. The stereochemical outcome of the reaction was explained by DFT calculations and the synthetic utility of the process was demonstrated by the gram‐scale transformation and formal synthesis of MK‐0731 as a kinesin spindle protein inhibitor.
Get selective! An efficient method for the enantioselective construction of β‐substituted β‐vinylglycinols by Pd‐catalyzed decarboxylative cycloaddition of vinylethylene carbonates 1 with isocyanates 2 was developed (see scheme).