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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
Tetrahedron: Asymmetry Pub Date : 28 February 2007 , DOI: 10.1016/j.tetasy.2006.12.028
Vicente J. Forrat , Diego J. Ramón , Miguel Yus

(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.

中文翻译:

可卡因滥用治疗剂(S)-(+)-1-(4- {2- [双(双(4-氟苯基)甲氧基]乙基}哌嗪-1-基)-2-苯基-2-)的第一催化对映选择性合成丙醇

S)-(+)-1-(4- {2- [双(4-氟苯基)甲氧基]乙基}哌嗪-1-基)-2-苯基-2-丙醇,可卡因是有前途的候选药物滥用治疗剂,需要准备几个步骤。关键的不对称步骤是在四异丙氧基钛存在下,通过使用不同的手性异冰片醇磺酰胺配体,将二甲基锌催化对映选择性加成至2-氯或2-溴乙酰苯。还提出了带有三氟甲基取代基的新的异冰片醇磺酰胺配体的合成及其在该加成中的用途。
更新日期:2017-01-31
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