Carbohydrate-Based Tolylsulfonyl Hydrazines: Effective Catalysts for Michael Addition of Indoles to Electron-Deficient Olefins in Water

Peng Wu; Yiqian Wan; Jiwen Cai

doi:10.1055/s-2008-1072735

LETTER

Carbohydrate-Based Tolylsulfonyl Hydrazines: Effective Catalysts for Michael Addition of Indoles to Electron-Deficient Olefins in Water

Peng Wu^a,b, Yiqian Wan^b, Jiwen Cai*^a,b
^a School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510080, P. R. of China
^b School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, P. R. of China
Fax: +86(20)87334718; e-Mail: puscjw@mail.sysu.edu.cn;

Abstract

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Abstract

Carbohydrate-based tolylsulfonyl hydrazines were used for the first time to catalyze the Michael reaction of indoles to electron-deficient olefins in aqueous media to afford 3-substituted indole derivatives in good to excellent yields at room temperature.

Key words

carbohydrate-based tolylsulfonyl hydrazines - catalyst - Michael addition of indole - water

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References

References and Notes

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Typical Experimental Procedure: A mixture of the olefin (1 mmol) and catalyst 1 (0.1 mmol) in H₂O (1 mL) was treated with indole (2 mmol). The resulting suspension was stirred at r.t. and the reaction was monitored by TLC until the starting material was consumed. The mixture was quenched with a sat. aq NaCl solution and then extracted with EtOAc (3 × 20 mL). The organic layers were combined and washed with brine, and dried over anhyd MgSO₄. The solvent was removed in vacuo to yield the crude product. Purification by silica gel chromatography using 100-200 mesh ZCX II eluted with hexane-EtOAc (5:1) afforded the Michael product.