ID | 48101 |
FullText URL | |
Author |
Irie, Shunsuke
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Abstract | Diastereoselective Ugi reactions of DMAP-based aldehydes with α-amino acids and tert-butyl isocyanide were examined. The reactions of 4-(dimethylamino)-2-pyridine-carboxaldehyde with various α-amino acids afforded 2-substituted DMAP derivatives with low diastereoselectivity. On the contrary, reactions with 4-(dimethylamino)-3-pyridine-carboxaldehyde delivered 3-substituted DMAP derivatives with moderate to high diastereoselectivity. The combination of α-amino acid and DMAP-based aldehyde is thus important to achieve high diastereoselectivity. Kinetic resolution of a secondary alcohol using a chiral DMAP derivative obtained through these reactions was also examined.
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Keywords | multicomponent reaction
Ugi reaction
chiral DMAP
kinetic resolution
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Published Date | 2011-10-20
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Publication Title |
Molecules
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Volume | volume16
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Issue | issue10
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Publisher | MDPI
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Start Page | 8815
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End Page | 8832
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ISSN | 1420-3049
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Content Type |
Journal Article
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Project |
Research Center of New Functional Materials for Energy Production, Storage, and Transport
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language |
English
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Copyright Holders | © 2011 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
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File Version | publisher
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Refereed |
True
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DOI | |
Web of Science KeyUT |