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Research Journals >
Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.45B [2006] >
IJC-B Vol.45B(12) December 2006] >
| Title: | Diastereoselective synthesis of 1,3-disubstituted 1,2,3,4 tetrahydro- -carbolines using Pictet-Spengler reaction in non-acidic aprotic media |
| Authors: | Sharma, S D
Bhaduri, Susmita
Kaur, Gurpreet |
| Keywords: | Pictet-Spengler reaction
-carbolines
diastereoselection
asymmetric synthesis
enantiopure |
| Issue Date: | Dec-2006 |
| Publisher: | CSIR |
| IPC Code: | Int.Cl.8 C07D |
| Abstract: | L-Tryptophan methyl ester hydrochloride 2 undergoes Pictet-Spengler reaction with aromatic aldehydes in non-acidic aprotic media to furnish tetrahydro--carbolines. The reaction proceeds in good yield and excellent diastereoselectivity giving cis isomers 4a-c and 6a as the major product. Use of an optically active aldehyde 10 for this reaction yields enantiopure cis-1,3-disubstituted 1,2,3,4-tetrahydro--carboline 11. |
| Page(s): | 2710-2715 |
| ISSN: | 0975-0983(Online); 0376-4699(Print) |
| Source: | IJC-B Vol.45B(12) December 2006]
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