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

页码：189 / 197

页数：9

共 36 条

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