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Synthesis 2017; 49(06): 1295-1300
DOI: 10.1055/s-0036-1588095
DOI: 10.1055/s-0036-1588095
paper
Asymmetric Allylation of 2-Oxocycloalkanecarboxylates
Further Information
Publication History
Received: 24 September 2016
Accepted: 21 October 2016
Publication Date:
24 November 2016 (online)
Abstract
In this study, the highly enantioselective α-allylation of α-substituted β-ketoesters, particularly 2-oxocycloalkanecarboxylates, is achieved by synergistic catalysis with an achiral palladium complex and a chiral primary amino acid. Various α-allylated β-ketoesters containing a quaternary carbon stereogenic center are synthesized in high yields (up to 97%) with excellent enantioselectivity (up to 99% ee).
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588095.
- Supporting Information
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For highly enantioselective catalytic asymmetric allylations of 2-oxocycloalkanecarboxylates, see:
For reviews on catalysis by combined use of organocatalysts and transition-metal catalysts, see:
For selected papers on allylations of α-branched carbonyl compounds by combined use of organocatalysts and transition-metal catalysts, see:
For O-silylated l-tyrosine, l-serines, and l-threonines, see:
For intramolecular Tsuji–Trost allylations, see: