Regioselective Ring-Opening of Amino Acid-Derived Chiral Aziridines: an Easy Access to cis-2,5-Disubstituted Chiral Piperazines

被引：27
|
作者：
Samanta, Krishnananda [1 ]
Panda, Gautam [1 ]
机构：
[1] Cent Drug Res Inst, Div Med & Proc Chem, Lucknow 226001, Uttar Pradesh, India
来源：
CHEMISTRY-AN ASIAN JOURNAL | 2011年 / 6卷 / 01期
关键词：
amino acids; cyclization; heterocycles; natural products; regioselectivity; MITSUNOBU; POTENT; INHIBITORS; CHEMISTRY;
D O I：
10.1002/asia.201000554
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient four-step synthetic strategy for cis-2,5-disubstituted chiral piperazines derived from amino-acid-based aziridines is described. The key steps in this strategy are the highly regioselective boron trifluoride diethyl etherate (BF3 center dot OEt2)-mediated ring-opening of less-reactive N-Ts chiral aziridines by alpha-amino acid methyl ester hydrochloride followed by Mitsunobu cyclization. This protocol has been used in an attempt to construct the piperazine core framework of natural product (+)-piperazinomycin.
引用
收藏
页码：189 / 197
页数：9
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