New biphenylic derivatives: synthesis, characterisation and enantiodiscrimination in chiral aggregates

被引：24

作者：

Andreani, R

Bombelli, C

Borocci, S

Lah, J

Mancini, G

Mencarelli, P

Vesnaver, G

Villani, C

机构：

[1] Univ Roma La Sapienza, CNR, Ist Metodol Chim Sez Meccan Reaz, Dipartimento Chim, I-00185 Rome, Italy

[2] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy

[3] Univ Tuscia, Dipartimento Sci Ambientali, I-01100 Viterbo, Italy

[4] Univ Ljubljana, Dept Chem, Ljubljana 1000, Slovenia

[5] Univ Roma La Sapienza, Dipartimento Chim & Tecnol Sostanze Biologicament, I-00185 Rome, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 06期

关键词：

D O I：

10.1016/j.tetasy.2004.01.038

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Chiral discrimination of racemic 2,2'-diamino-6-(octanoyloxymethyl)biphenyl and 2,3'-diamino-6-(octanoyloxymethyl)biphenyl in micelles formed either by N-alkyl-NN-dimethyl-N-(S)-(1-phenyl)ethylammonium bromide or sodium N-dodecanoyl-L-prolinate has been investigated by H-1 NMR spectroscopy. The rotational barrier of 2,3'-diamino-6-(octanoyloxymethyl)biphenyl has been evaluated by HPLC and by dynamic NMR. The rotational barrier of 2,3-diamino-6-(acetoxymethyl)biphenyl was evaluated by theoretical calculations and compared with the experimental data relative to its analogue. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：987 / 994

页数：8

共 37 条

[11] Deracemization of an axially chiral biphenylic structure in chiral micellar aggregates [J].