Enantioselective inclusion of (R)-phenylglycyl-(R)-phenylglycine with benzyl methyl sulfoxides

被引：13

作者：

Akazome, M

Hirabayashi, A

Ogura, K

机构：

[1] Chiba Univ, Fac Engn, Dept Mat Technol, Chiba 2638522, Japan

[2] Chiba Univ, Grad Sch Sci & Technol, Chiba 2638522, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 52期

关键词：

inclusion compounds; peptides; sulfoxides; enatiomeric recognition; guest exchange;

D O I：

10.1016/j.tet.2004.10.032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A crystalline dipeptide, (R)-phenylglycyl-(R)-phenylglycine (RR-1), recognized p-halobenzyl methyl sulfoxides with high R-enantioselectivity (86-99% ee) to form inclusion compounds. The single-crystal X-ray analyses showed that RR-1 molecules are arranged in parallel and zigzags via hydrogen bonding to construct a pleated sheet. The guest molecules that form hydrogen bond with +NH3 of RR-1 are accommodated in the channel cavity between the layers. In contrast to the inclusion crystals of parent benzyl methyl sulfoxide, in which a rectangular cavity is formed, the cavity including p-halobenzyl methyl sulfoxides becomes rhomboidal. We also examine the guest exchange in these inclusion compounds and it was found that the guest exchanges occur when the host structure changes. (C) 2004 Published by Elsevier Ltd.

引用

页码：12085 / 12093

页数：9

共 56 条

[1] Enantiomeric inclusion of α-hydroxy esters by (R)-(1-naphthyl)glycyl-(R)-phenylglycine and the crystal structures of the inclusion cavities [J].