Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 52, Pages 12749-12753Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201703479
Keywords
amino acids; asymmetric synthesis; imino esters; organocatalysis; umpolung
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Funding
- Research Promotion on SIS (the Society of Iodine Science)
- General Sekiyu R & D Encouragement Assistance Foundation
- Leading Research Promotion Program Soft Molecular Activation of Chiba University, Japan
- Grants-in-Aid for Scientific Research [16H04144, 17K19114] Funding Source: KAKEN
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The catalytic asymmetric umpolung reaction of ketimines is of great importance, because it can easily provide chiral amines bearing a tetrasubstituted carbon atom on its asymmetric center. Because amino acids with a tetrasubstituted carbon center are useful due to their wide applicability as pharmaceuticals and chiral building blocks, their enantioselective synthesis has great significance in organic synthesis. Herein, we demonstrate a metal-free novel phase-transfer-catalyzed highly regio- and enantioselective umpolung Michael reaction of alpha-imino esters, which provides amino acid derivatives in high yields with up to 98% ee. The products are successfully converted into chiral amino acid derivative and delta-lactone with high enantiopurity.
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