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Hydroxytetraphenylenes as Chiral Ligands: Application to Asymmetric Darzens Reaction of Diazoacetamide with Aldehydes

Guo-Li Chai, Jian-Wei Han, Henry N. C. Wong*

*Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, P. R. of China, Email: hncwongcuhk.edu.hk

G.-L. Chai, J.-W. Han, H. N. C. Wong, Synthesis, 2017, 49, 181-187.

DOI: 10.1055/s-0036-1588880 (free Supporting Information)


Abstract

A chiral titanium complex formed in situ from Ti(OiPr)4 and chiral 1,16-dihydroxytetraphenylene with rigid conformation enables highly diastereo- and enantioselective Darzens reactions between aldehydes and diazo-N,N-dimethylacetamide to provide cis-glycidic amides in good yields with excellent enantiomeric purities.

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Key Words

Darzens Reaction, asymmetric catalysis, tetraphenylene, chiral ligand, diazoacetamide, epoxides


ID: J66-Y2017