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Title: Diastereoselective synthesis of 1,3-disubstituted 1,2,3,4 tetrahydro-<img src='/image/spc_char/beta.gif' border=0>-carbolines using Pictet-Spengler reaction in non-acidic aprotic media
Authors: Sharma, S D
Bhaduri, Susmita
Kaur, Gurpreet
Keywords: Pictet-Spengler reaction
<img src='/image/spc_char/beta.gif' border=0>-carbolines
asymmetric synthesis
Issue Date: Dec-2006
Publisher: CSIR
Series/Report no.: Int.Cl.<sup>8</sup> C07D
Abstract: <sub>L</sub>-Tryptophan methyl ester hydrochloride <b style="">2</b> undergoes Pictet-Spengler reaction with aromatic aldehydes in non-acidic aprotic media to furnish tetrahydro-<img src='/image/spc_char/beta.gif' border=0>-carbolines. The reaction proceeds in good yield and excellent diastereoselectivity giving <i style="">cis</i> isomers <b style="">4a-c</b> and <b style="">6a</b> as the major product. Use of an optically active aldehyde <b style="">10</b> for this reaction yields enantiopure <i style="">cis</i>-1,3-disubstituted 1,2,3,4-tetrahydro-<img src='/image/spc_char/beta.gif' border=0>-carboline <b style="">11</b>.
Description: 2710-2715
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.45B(12) December 2006]

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