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Synthesis 2017; 49(01): 181-187
DOI: 10.1055/s-0036-1588880
DOI: 10.1055/s-0036-1588880
paper
Hydroxytetraphenylenes as Chiral Ligands: Application to Asymmetric Darzens Reaction of Diazoacetamide with Aldehydes
Further Information
Publication History
Received: 10 August 2016
Accepted after revision: 22 August 2016
Publication Date:
15 September 2016 (online)
Dedicated to Professor Dr. Dieter Enders on the occasion of his 70th birthday.
Abstract
Hydroxytetraphenylenes with rigid conformations are potential candidates for employment as chiral ligands in asymmetric synthesis. Highly diastereo- and enantioselective Darzens reactions between aldehydes and diazo-N,N-dimethylacetamide were found to be catalyzed by a chiral titanium complex formed in situ from Ti(O i Pr)4 and chiral 1,16-dihydroxytetraphenylene, leading to the formation of cis-glycidic amides in moderate to high yields with excellent enantiomeric purities (40–99% yield, up to 99% ee).
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588880.
- Supporting Information
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