First catalytic enantioselective synthesis of the cocaine abuse therapeutic agent (S)-(+)-1-(4-{2-[bis(4-fluorophenyl)methoxy]ethyl}-piperazin-1-yl)-2-phenyl-2-propanol

被引：23
作者：
Forrat, Vicente J. [1 ]
Ramon, Diego J. [1 ]
Yus, Miguel [1 ]
机构：
[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, ISO, E-03080 Alicante, Spain
来源：
TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 03期
关键词：
D O I：
10.1016/j.tetasy.2006.12.028
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
(S)-(+)-1-(4-{2-[Bis(4-fluorophenyl)methoxy]ethyl} piperazin-1-yl)-2-phenyl-2-propanol, which is a promising candidate as a cocaine abuse therapeutic agent, is prepared in several steps. The key asymmetric step is the catalytic enantioselective addition of dimethylzinc to either 2-chloro or 2-bromoacetophenone catalyzed by the use of different chiral isoborneolsulfonamide ligands in the presence of titanium tetraisopropoxide. The synthesis of a new isoborneolsulfonamide ligand bearing a trifluromethyl. substituent and its use in this addition is also presented. (c) 2007 Elsevier Ltd. All rights reserved.
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收藏
页码：400 / 405
页数：6
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