Carbonylative enantioselective meso-desymmetrization of cis-epoxides to trans-β-lactones: effect of salen-ligand electronic variation on enantioselectivityElectronic supplementary information (ESI) available: Experimental procedures, characterization data for all new compounds, expanded Tables S1-S4. See DOI: 10.1039/c4cc04397a

Carbonylation catalysts for the desymmetrization of meso -epoxides yielding enantioenriched trans -β-lactones are reported. Fine-tuning the electronic properties of the ligand further improved enantioselectivity. The sterics of the substrate dictated whether a given electronic variation decreased or...

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Main Authors: Mulzer, Michael, Lamb, Jessica R, Nelson, Zachary, Coates, Geoffrey W
Format: Article
Language:English
Online Access:Get full text
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Summary:Carbonylation catalysts for the desymmetrization of meso -epoxides yielding enantioenriched trans -β-lactones are reported. Fine-tuning the electronic properties of the ligand further improved enantioselectivity. The sterics of the substrate dictated whether a given electronic variation decreased or increased enantioenrichment, revealing an unexpected relationship between the substrate's steric environment and the electronic nature of the optimal catalyst. Carbonylation catalysts for the desymmetrization of meso -epoxides yielding enantioenriched trans -β-lactones are reported.
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc04397a