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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
asymmetric synthesis
Issue Date: Dec-2006
Publisher: CSIR
IPC CodeInt.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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