ja7b07983_si_001.pdf (5.18 MB)
Cobalt-Catalyzed Carbonylative Cross-Coupling of Alkyl Tosylates and Dienes: Stereospecific Synthesis of Dienones at Low Pressure
journal contribution
posted on 2017-08-22, 00:00 authored by Brendon
T. Sargent, Erik J. AlexanianDespite advances in organometallic
cross-coupling of alkyl electrophiles,
there are few stereoselective reactions of chiral, nonracemic substrates.
Herein we report a stereospecific carbonylative coupling of alkyl
tosylates and dienes producing enantioenriched dienones. This catalytic
process proceeds under low pressure and mild conditions using a simple
cobalt catalyst and extends to diverse tosylate and diene coupling
partners. The transformation constitutes a unique, convergent approach
to the asymmetric synthesis of valuable carbonyl compounds from easily
accessed starting materials.
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Keywords
Alkyl Tosylatesorganometallic cross-couplingLow Pressuredienenonracemic substratessynthesisconvergent approachStereospecific Synthesistransformationstereospecific carbonylativealkyl tosylatesmaterialcobalt catalystDienonecarbonyl compoundsstereoselective reactionsadvanceenantioenriched dienoneschiralHereinDieneprocess proceedsalkyl electrophilesCobalt-Catalyzed Carbonylative Cross-Coupling
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