STEREOSELECTIVE SYNTHESIS OF PSEUDOGLYCAL C-GLYCOSIDES VIA TRICHLOROACETIMIDATE ACTIVATION OF GLYCALS^a

Adel A.-H. Abdel-Rahman Department of Chemistry, Universiy of Konstanz, Fach M 725, Konstanz, D-78457, Germany

Mohamed Takhi Department of Chemistry, Universiy of Konstanz, Fach M 725, Konstanz, D-78457, Germany

El Sayed H. El Ashry Department of Chemistry, Faculty of Science, Univesity of Alexandria, Alexandria, Egypt

Richard R. Schmidt Department of Chemistry, Universiy of Konstanz, Fach M 725, Konstanz, D-78457, GermanyCorrespondence[email protected]

Abstract

A variety of functionalized pseudoglycal C-glycosides (C-pseudoglycals or C-hex-2-enopyranosides) have been obtained in excellent yield and stereoselectivity from the trimethylsilyl triflate (Me ₃SiOTf) catalyzed reaction of trichloroacetimidate derivative 2 with silylated nucleophiles such as allyl and propargyl silanes and silyl enol ethers.

^a Dedicated to Prof. Joachim Thiem on the occasion of his 60th birthday.

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ACKNOWLEDGMENTS

This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie. A. A.-H. A.-R. is grateful for an Alexander von Humboldt-Fellowship.

Notes

^a Dedicated to Prof. Joachim Thiem on the occasion of his 60th birthday.

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STEREOSELECTIVE SYNTHESIS OF PSEUDOGLYCAL C-GLYCOSIDES VIA TRICHLOROACETIMIDATE ACTIVATION OF GLYCALS^a

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STEREOSELECTIVE SYNTHESIS OF PSEUDOGLYCAL C-GLYCOSIDES VIA TRICHLOROACETIMIDATE ACTIVATION OF GLYCALSa

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STEREOSELECTIVE SYNTHESIS OF PSEUDOGLYCAL C-GLYCOSIDES VIA TRICHLOROACETIMIDATE ACTIVATION OF GLYCALS^a