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Efficient and Versatile Modification of the Secondary Face of Cyclodextrins through Copper‐Catalyzed Huisgen 1,3‐Dipolar Cycloaddition
Author(s) -
Ward Sandra,
Ling ChangChun
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100445
Subject(s) - chemistry , cycloaddition , amide , click chemistry , 1,3 dipolar cycloaddition , combinatorial chemistry , alkyl , copper , alcohol , organic chemistry , catalysis , polymer chemistry
The perfunctionalization of the secondary face of cyclodextrins (CDs) is a challenging task that often results in poor yields. Here, we report that the use of copper‐catalyzedHuisgen 1,3‐dipolar cycloaddition is an efficient and versatile strategy that provides perfunctionalized CDs at the secondary face with good to high yields. A variety of functional groups, such as alkyl, alkenyl, ester, carboxylic acid, amide, and alcohol, have been successfully incorporated on the secondary face of β‐CD from the same starting material. These functionalized CD derivatives could be used as building blocks for further structural modification or as hosts for different applications.