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ID 48101
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Author
Mandai, Hiroki ORCID Kakenhi publons
Irie, Shunsuke
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.
Keywords
multicomponent reaction
Ugi reaction
chiral DMAP
kinetic resolution
Published Date
2011-10-20
Publication Title
Molecules
Volume
volume16
Issue
issue10
Publisher
MDPI
Start Page
8815
End Page
8832
ISSN
1420-3049
Content Type
Journal Article
Project
Research Center of New Functional Materials for Energy Production, Storage, and Transport
language
英語
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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Refereed
True
DOI
Web of Sience KeyUT