A One‐Pot, Copper‐Catalyzed Cascade Route to 2‐Indolyl‐C‐glycosides1. Issue 3 (30th November 2012)

• Record Type: Journal Article
• Authors: Subramanian, Parthasarathi; Kaliappan, Krishna P.
• Is Part Of: European journal of organic chemistry. Issue 3(2013)
• Page Start: 595
• Page End: 604
• Publication Date: 2012-11-30
• Subjects: Carbohydrates -- C‐glycosides -- Nitrogen heterocycles -- Alkynes -- Copper -- Domino reactions; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201201208
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: An efficient and high‐yielding, one‐pot, Cu‐catalyzed synthesis of 2‐indolyl‐C‐glycosides is delineated. The sequence involves a cascade Sonogashira type coupling and a hydroamination reaction between sugar‐derived alkynes and N ‐tosyl‐ o ‐iodoaniline followed by removal of the N ‐tosyl group to provide a library of 2‐indolyl‐C‐glycosides in moderate to excellent yields. Abstract : An efficient and high‐yielding, one‐pot, Cu‐catalyzed synthesis of 2‐indolyl‐C‐glycosides is delineated. The sequence involves a cascade Sonogashira type coupling and a hydroamination reaction between sugar‐derived alkynes and N ‐tosyl‐ o ‐iodoaniline followed by the removal of the N ‐tosyl group to provide a library of 2‐indolyl‐C‐glycosides in moderate to excellent yields.