Selective Derivation of (-)-Methyl-3-dehydroshikimate with Hydrazine Compounds

doi:10.7503/cjcu20120263

Chem. J. Chinese Universities ›› 2012, Vol. 33 ›› Issue (10): 2223.doi: 10.7503/cjcu20120263

• Organic Chemistry • Previous Articles Next Articles

Selective Derivation of (-)-Methyl-3-dehydroshikimate with Hydrazine Compounds

WU Wei^1,2, ZHANG En-Sheng^1,2, WEI Wen¹, HUANG Tong-Kun¹, LIU Xin-Wei³, YANG Shao-Fan³, ZOU Yong¹

1. Guangzhou Institute of Chemistry, Chinese Academy of Science, Guangzhou 510650, China;
2. Graduate School of Chinese Academy of Sciences, Beijing 100049, China;
3. Guangxi Wanshan Spice Co., Ltd., Lingshan 535400, China

Received:2012-03-22 Online:2012-10-10 Published:2012-09-12

Abstract

Abstract:

The purpose of this paper is to achieve the high value-added and diversified transformation of the renewable biomass (-)-shikimic acid, starting from which, the key intermediate (-)-methyl-3-dehydroshikimiate was readily obtained through esterification and 2-iodoxybenzoic acid-oxidation. The reaction of (-)-methyl-3-dehydroshikimiate with hydrazine, acethydrazide, hydrazinobenzene and acetamide could give rise to non-aromatization products(2a and 2d), partial-aromatization products(2b) and aromatization products(2c and 2e) selectively under different conditions. The present methodology with good diversity, high selectivity and operational simplicity provides a new paradigm for the transformation of bio-based and non-food feedstock.

Key words: (-)-Methyl-3-dehydroshikimate, Hydrazine compound, Selectivity, Renewable source

CLC Number:

O629.9

TrendMD:

WU Wei, ZHANG En-Sheng, WEI Wen, HUANG Tong-Kun, LIU Xin-Wei, YANG Shao-Fan, ZOU Yong. Selective Derivation of (-)-Methyl-3-dehydroshikimate with Hydrazine Compounds[J]. Chem. J. Chinese Universities, 2012, 33(10): 2223.

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Selective Derivation of (-)-Methyl-3-dehydroshikimate with Hydrazine Compounds

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