Journal
TETRAHEDRON LETTERS
Volume 56, Issue 25, Pages 3890-3893Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.04.107
Keywords
Quaternary carbon; Organocatalysis; Asymmetric synthesis; Primary amino acid; Ketoaldehyde
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Funding
- MEXT, Japan (KAKENHI) [24105501]
- Toyohashi University of Technology
- National College of Technology
- Grants-in-Aid for Scientific Research [26105728, 24105501, 26105701] Funding Source: KAKEN
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Synthesis of 5-ketoaldehydes possessing a highly stereo-controlled all-carbon quaternary stereogenic center was achieved by organocatalytic asymmetric Michael addition of alpha-branched aldehydes to vinyl ketones. A readily obtainable primary amino acid, L-phenylalanine, proved an effective catalyst for this reaction to give the 5-ketoaldehydes with high enantioselectivities (up to 95% ee). (C) 2015 Elsevier Ltd. All rights reserved.
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