Abstract
(matrix presented) R1, R2 = (-OCH2CH2-), (-OCH2CH2CH2-), (-CH=CH-CH2-), (-OCH2CH3, H) (R,R)-3-Aza-3-benzyl-1,5-dihydroxy-1,5-diphenylpentane (1) ligated Ti(IV) complex (1-TiCl2) is used as a chiral Lewis acid catalyst for promoting asymmetric IED Diels-Alder reaction between electron-rich dienophiles and electron-poor dienes. Here we introduce a facile route for the synthesis of asymmetric tetrahydroquinoline derivatives using the above-mentioned chiral catalyst reagent in the presence of 4 Å molecular sieves. The reactions proceed with moderate yields and at times high enantioselectivty.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1973-1976 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 3 |
| Issue number | 13 |
| DOIs | |
| State | Published - Jun 28 2001 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Sundararajan, G., Prabagaran, N., & Varghese, B. (2001). First Asymmetric Synthesis of Quinoline Derivatives by Inverse Electron Demand (IED) Diels-Alder Reaction Using Chiral Ti(IV) Complex. Organic Letters, 3(13), 1973-1976. https://doi.org/10.1021/ol0159221