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Synthesis 2010(3): 403-406  
DOI: 10.1055/s-0029-1217122
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© Georg Thieme Verlag Stuttgart ˙ New York

A Facile Chiral Pool Synthesis of (S)-6-Nitroindoline-2-carboxylic Acid from l-Phenylalanine

Jin-Qiang Liu, Chao Qian*, Xin-Zhi Chen
Department of Chemical Engineering, Zhejiang University, Hangzhou 310027, P. R. of China
Fax: +86(571)87951615; e-Mail: supmoney@163.com;
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Publikationsverlauf

Received 28 August 2009
Publikationsdatum:
13. November 2009 (online)

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A Facile Chiral Pool Synthesis of (S)-6-Nitroindoline-2-carboxylic Acid from l-PhenylalanineSynthesis 2010; 2010(03): e1-e1
DOI: 10.1055/s-0029-1218648

Abstract

(S)-6-Nitroindoline-2-carboxylic acid, a substructure occurring in numerous biologically active natural products, was synthesized with moderate yield (53%) and high enantiomeric excess (>99.5%) starting from the nitration of l-phenylalanine, which is a commercially available chiral pool compound, followed by successively bromination and intramolecular cyclization. The route was carried out in gram quantities and it is suitable for industrial application due to its convenient reaction conditions and low cost.

Key words

chiral pool synthesis - (S)-6-nitroindoline-2-carboxylic acid - l-phenylalanine - 2-bromo-4-nitro-l-phenylalanine - intramolecular cyclization

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