2011年10月
Studies on the Synthesis of DMAP Derivatives by Diastereoselective Ugi Reactions
MOLECULES
- ,
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- 巻
- 16
- 号
- 10
- 開始ページ
- 8815
- 終了ページ
- 8832
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.3390/molecules16108815
- 出版者・発行元
- MDPI
Diastereoselective Ugi reactions of DMAP-based aldehydes with alpha-amino acids and tert-butyl isocyanide were examined. The reactions of 4-(dimethylamino)-2-pyridine-carboxaldehyde with various alpha-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 alpha-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.
- リンク情報
- ID情報
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- DOI : 10.3390/molecules16108815
- eISSN : 1420-3049
- Web of Science ID : WOS:000296973000046