Site-selective hexa-hetero-functionalization of α-cyclodextrin an archetypical C₆-symmetric concave cycle.

Wang, Bo; Zaborova, Elena; Guieu, Samuel; Petrillo, Marta; Guitet, Maxime; Blériot, Yves; Ménand, Mickaël; Zhang, Yongmin et al. · Nat Commun · 2014

basic_science · Level V

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Abstract

Access to Cn (n>4) symmetric cyclic concave molecules with a different function on each of their n subunits is an unmet challenge. The reason lies in the lack of a post-functionalization method whose site selectivity is sufficiently understood, predictable and modulable to access most functionalization patterns. Here we disclose a new site-directing rule for a debenzylation reaction on cyclodextrins that solves this problem and allows the unprecedented access to penta- and ultimately hexa-differentiations of such C6 concave cycles. This achievement opens the access to objects with very high-density information.