Copper-Catalyzed Asymmetric Allylic Alkylation of Halocrotonates: Efficient Synthesis of Versatile Chiral Multifunctional Building Blocks

The highly enantioselective synthesis of α‐methyl‐substituted esters is reported in up to 90% yield and up to 99% ee using copper‐TaniaPhos as chiral catalyst. The transformation proved scalable to at least 6.6 mmol (1.7 g scale). The products of this transformation have been further elaborated to m...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2010-04, Vol.352 (6), p.999-1013
Main Authors: den Hartog, Tim, Maciá, Beatriz, Minnaard, Adriaan J., Feringa, Ben L.
Format: Article
Language:English
Subjects:
asymmetric catalysis
Asymmetry
Branched
carbon-carbon bond formation
Catalysis
copper catalysis
Dimethyl
Esters
Grignard reagents
Lactones
multifunctional building blocks
Synthesis
Transformations
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Summary:The highly enantioselective synthesis of α‐methyl‐substituted esters is reported in up to 90% yield and up to 99% ee using copper‐TaniaPhos as chiral catalyst. The transformation proved scalable to at least 6.6 mmol (1.7 g scale). The products of this transformation have been further elaborated to multifunctional building blocks with a single (branched esters and acids) or multiple stereogenic centers (vicinal dimethyl esters, as well as, hydroxy‐ or iodo‐substituted lactones).
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201000109