Simultaneously bound guests and chiral recognition: a chiral self-assembled supramolecular host encapsulates hydrophobic guests

TETRAHEDRON

卷:64

Article

Hastings, Courtney J.^1,2  Pluth, Michael D.^1,2  Biros, Shannon M.^1,2  Bergman, Robert G.^1,2  Raymond, Kenneth N.^1,2 

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

[2] Lawrence Berkeley Natl Lab, Div Chem, Berkeley, CA 94720 USA

关键词: supramolecular chemistry;    chiral recognition;    aromatic guests;    simultaneous encapsulation;   

DOI  :  10.1016/j.tet.2008.05.131

来源: Elsevier

【 摘 要 】

Driven by the hydrophobic effect, a water-soluble, chiral, self-assembled supramolecular host is able to encapsulate hydrophobic Organic guests in aqueous solution. Small aromatics can be encapsulated in the supramolecular assembly, and the simultaneous encapsulation of multiple species is observed in many cases. The molecular host assembly is able to recognize different substitutional isomers of disubstituted benzenes with ortho substitution leading to the encapsulation of two guests, but meta or para substitution leading to the encapsulation of only one guest. The scope of hydrophobic guest encapsulation is further explored with chiral natural products. Upon encapsulation of chiral molecules into the racemic host, diastereomeric host-guest complexes are formed with observed diastereoselectivities of up to 78:22 in the case of fenchone. (C) 2008 Elsevier Ltd. All rights reserved.

【 授权许可】

Free