Synlett 2013; 24(20): 2629-2640
DOI: 10.1055/s-0033-1339877
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© Georg Thieme Verlag Stuttgart · New York

Site-Selective Heterofunctionalization of Cyclodextrins: Discovery, Development, and Use in Catalysis

Matthieu Sollogoub*
UPMC Univ. Paris 06, Sorbonne Universités, Institut Universitaire de France, LabEx MiChem, IPCM, UMR CNRS 7201, C181, 4 Place Jussieu, F-75005 Paris, France   Fax: +33(1)44275504   Email: matthieu.sollogoub@upmc.fr
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Publication History

Received: 16 July 2013

Accepted after revision: 03 September 2013

Publication Date:
14 October 2013 (online)


Abstract

To fulfill the promise offered by concave molecules such as cyclodextrins, there is a desperate need for efficient methods for multiple heterofunctionalization. We have developed several strategies for preparing heterofunctionalized cyclodextrins based on a newly discovered regioselective debenzylation reaction of sugars and an understanding of its mechanism. Bascule bridging and tandem azide reduction–deprotection are two complementary ways of attaining an unprecedented degree of complexity of functionalization of the primary rim of cyclodextrins, permitting access to a diverse library of functionalized cyclodextrins. The resulting complex structures have a number of applications in a wide range of areas. We have explored some of these, such as asymmetric catalysis using regioisomers to induce enantioselectivity or very high turnover numbers, but it is our firm belief that this methodology opens many other possibilities.

 
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