Enantioselective Iridium-Catalyzed Vinylogous Reformatsky-Aldol Reaction from the Alcohol Oxidation Level: Linear Regioselectivity by Way of Carbon-Bound Enolates

Enantioselective Iridium-Catalyzed Vinylogous Reformatsky-Aldol Reaction from the Alcohol Oxidation Level: Linear Regioselectivity by Way of Carbon-Bound Enolates

Reformatsky reinvented: Highly enantioselective vinylogous Reformatsky‐type addition has been achieved from the alcohol oxidation level with linear regioselectivity through carbon‐bound enolates (see scheme; Boc=tert‐butoxycarbonyl). Complete levels of catalyst‐directed diastereoselectivity are obse...

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Veröffentlicht in:Angewandte Chemie International Edition 2011-04, Vol.50 (15), p.3493-3496
Hauptverfasser: Hassan, Abbas, Zbieg, Jason R., Krische, Michael J.
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemistry
Aldehydes
aldol reaction
allylation
Catalysis
homogeneous catalysis
iridium
Iridium - chemistry
Molecular Structure
Stereoisomerism
transfer hydrogenation
Vinyl Compounds - chemistry
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Zusammenfassung:Reformatsky reinvented: Highly enantioselective vinylogous Reformatsky‐type addition has been achieved from the alcohol oxidation level with linear regioselectivity through carbon‐bound enolates (see scheme; Boc=tert‐butoxycarbonyl). Complete levels of catalyst‐directed diastereoselectivity are observed in the reaction of an α‐chiral alcohol.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201100646