Catalytic Dynamic Kinetic Resolutions with N-Heterocyclic Carbenes: Asymmetric Synthesis of Highly Substituted β-Lactones

New DKR type: An N‐heterocyclic carbene (NHC)‐catalyzed dynamic kinetic resolution of racemic α‐substituted β‐keto esters has been developed. This method relies on the epimerization of an NHC‐enol intermediate before subsequent aldol/acylation events. Highly substituted β‐lactones are produced in go...

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Veröffentlicht in:	Angewandte Chemie International Edition 2012-07, Vol.51 (29), p.7309-7313
Hauptverfasser:	Cohen, Daniel T., Eichman, Chad C., Phillips, Eric M., Zarefsky, Emily R., Scheidt, Karl A.
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes - chemical synthesis Aldehydes - chemistry aldols asymmetric synthesis Catalysis Cyclopentanes - chemical synthesis dynamic kinetic resolution Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry homoenolates Kinetics Lactones - chemical synthesis Lactones - chemistry Methane - analogs & derivatives Methane - chemical synthesis Methane - chemistry N-heterocyclic carbenes Stereoisomerism
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Beschreibung
Zusammenfassung:	New DKR type: An N‐heterocyclic carbene (NHC)‐catalyzed dynamic kinetic resolution of racemic α‐substituted β‐keto esters has been developed. This method relies on the epimerization of an NHC‐enol intermediate before subsequent aldol/acylation events. Highly substituted β‐lactones are produced in good yield with good to excellent selectivities (see scheme).
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201203382