N/N/O versus N/O/O and N/O amino isoborneols in the enantioselective ethylation of benzaldehyde

被引：12
作者：
Engel, Tomas de las Casas [1 ]
Maroto, Beatriz Lora [1 ]
Martinez, Antonio Garcia [1 ]
Cerero, Santiago de la Moya [1 ]
机构：
[1] Univ Complutense Madrid, Dept Quim Organ 1, Fac Ciencias Quim, E-28040 Madrid, Spain
来源：
TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 03期
关键词：
D O I：
10.1016/j.tetasy.2008.01.012
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Enantiopure 10-(4-methylpiperazin-1-yl)isoborneol, a N/N/O-tridentate chiral diamino isoborneol, has been obtained from enantiopure ketopinic acid and its catalytic activity (as chiral ligand in the enantioselective addition of diethylzinc to benzaldehyde) measured and compared with the previously reported data for related N/N/O, N/O/O, and N/O isoborneols. It is demonstrated that the pentacoordinated-zinc Oppolzer's model for transition states is useful for explaining the catalytic behavior of N/N/O-tridentate ligands. In such cases, stable syn- or anti-type transition states can be proposed depending on the catalyst's conformational flexibility. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：269 / 272
页数：4
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