Abstract
A highly efficient synthetic approach to unnatural chiral β-Ar,Ar′-α-amino acid esters bearing two contiguous stereogenic centers has been developed. The first enantioselective 1,6-conjugate addition of glycine Schiff bases to para-quinone methides was achieved using a Cu(CH3CN)4BF4/Ph-Foxap catalytic system (1 mol %). The reaction proceeded smoothly to generate corresponding products in high yields with excellent diastereoselectivities (up to 99:1) and enantioselectivities (up to >99% ee). Subsequent reduction delivered enantiopure unnatural amino alcohols, which were utilized for the synthesis of novel chiral ligands.
Original language | English |
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Pages (from-to) | 652-656 |
Number of pages | 5 |
Journal | ACS Catalysis |
Volume | 6 |
Issue number | 2 |
Early online date | 23 Dec 2015 |
DOIs | |
Publication status | Published - 28 Dec 2015 |
Keywords
- asymmetric catalysis
- conjugate addition
- copper
- para-quinone methides
- unnatural α-amino acids
ASJC Scopus subject areas
- Catalysis