Synthesis resolution of 3,4,3'4'-tetramethoxyl-1,1'-1,2,3,4-tetrahydrobisisoquinoline and application in asymmetric alkylation reactions
This report describes the synthesis of chiral 3,4,3',4'-tetramethoxyl-1,1'-1,2,3,4-tetrahydrobisisoquinoline. The compound is to be later used as a catalyst in the asymmetric alkylation addition reaction between 2-propargyl acetate and benzaldehyde to form an allylic alcohol. Racemic...
Saved in:
| Main Author: | |
|---|---|
| Other Authors: | |
| Format: | Final Year Project |
| Language: | English |
| Published: |
2009
|
| Subjects: | |
| Online Access: | http://hdl.handle.net/10356/16572 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Institution: | Nanyang Technological University |
| Language: | English |
| Summary: | This report describes the synthesis of chiral 3,4,3',4'-tetramethoxyl-1,1'-1,2,3,4-tetrahydrobisisoquinoline. The compound is to be later used as a catalyst in the asymmetric alkylation addition reaction between 2-propargyl acetate and benzaldehyde to form an allylic alcohol.
Racemic 3,4,3',4'-tetramethoxyl-1,1'-1,2,3,4-tetrahydrobisisoquinoline was obtained via a three step procedure : First an oxyamide was formed through a reaction between 2(3,4 methoxyphenyl)ethylamine followed by cyclicization of the oxyamide via a Bischler Napieralski reaction and reduction by NaBH4 (Polniaszek’s method).
The resulting racemic compound was resolved using (S)-(+)-α-methylbenzyl isocyanate as the resolving agent. A pure diastreomer was obtained through recrystallization in ethanol the diastereomer was then alcoholised under sodium butoxide to give the desired biiisisoquinoline. |
|---|