亲核试剂导向的顺式-1-对甲苯磺酰基-2-对甲苯磺酰氧基甲基-3-(三氟甲基)氮杂环丙烷选择性转化为氮杂环丙烷、氮杂环丁烷和苯并稠合的二硫杂环戊烷、氧杂硫杂环戊烷、二氧杂环己烷和(硫代)吗啉。
Nucleophile-directed selective transformation of cis-1-tosyl-2-tosyloxymethyl-3-(trifluoromethyl)aziridine into aziridines, azetidines, and benzo-fused dithianes, oxathianes, dioxanes, and (thio)morpholines.
机构信息
Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium.
出版信息
Chemistry. 2013 May 3;19(19):5966-71. doi: 10.1002/chem.201204485. Epub 2013 Mar 19.
A five-step procedure for the synthesis of cis-1-tosyl-2-tosyloxymethyl-3-(trifluoromethyl)aziridine was developed, starting from 1-ethoxy-2,2,2-trifluoroethanol, involving imination, aziridination, ester reduction, hydrogenation, and N-,O-ditosylation steps. Further synthetic elaborations revealed a remarkable difference in the reactivity of cis-1-tosyl-2-tosyloxymethyl-3-(trifluoromethyl)aziridine with respect to aromatic sulfur and oxygen nucleophiles, thus enabling the selective deployment of this versatile substrate as a building block for the synthesis of functionalized aziridines, azetidines, and benzo-fused dithianes, oxathianes, dioxanes, and (thio)morpholines.
开发了一种从 1-乙氧基-2,2,2-三氟乙醇出发，经过亚胺化、氮杂环丙烷化、酯还原、氢化和 N,O-二对甲苯磺酰化步骤，合成顺式-1-对甲苯磺酰基-2-对甲苯磺酰氧基甲基-3-(三氟甲基)氮杂环丙烷的五步法。进一步的合成研究揭示了顺式-1-对甲苯磺酰基-2-对甲苯磺酰氧基甲基-3-(三氟甲基)氮杂环丙烷与芳香族硫和氧亲核试剂反应性的显著差异，从而使这种多功能底物能够作为合成功能化氮杂环丙烷、氮杂环丁烷和苯并稠合二硫杂环戊烷、氧杂环戊烷、二氧六环和（硫）吗啉的构建块进行选择性应用。
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