Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 47, Pages 15303-15306Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b10099
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Funding
- National Sciences and Engineering Research Council (NSERC)
- Queen's University
- NSERC
- Government of Ontario
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A highly enantioselective rhodium-catalyzed allylic alkylation of prochiral alpha,alpha-disubstituted aldehyde enolates with allyl benzoate is described. This protocol provides a novel approach for the synthesis of acyclic quaternary carbon stereogenic centers and it represents the first example of the direct enantioselective alkylation of an aldehyde enolate per se. The versatility of the alpha-quaternary aldehyde products is demonstrated through their conversion to a variety of useful motifs applicable to target-directed synthesis. Finally, mechanistic studies indicate that high levels of asymmetric induction are achieved from a mixture of prochiral (E)- and (Z)-enolates, which provides an exciting development for this type of transformation.
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