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Mild non-transition metal catalyzed deprotection of N-allyloxycarbonyl amines
Tetrahedron Letters ( IF 1.5 ) Pub Date : 20 June 2005 , DOI: 10.1016/j.tetlet.2005.04.064
Ronald H. Szumigala , Ekama Onofiok , Sandor Karady , Joseph D. Armstrong , Ross A. Miller

A synthesis of methyl (2S)-2-amino-4-oxo-2,4-diphenylbutanoate has been achieved via a novel one-pot non-transition metal mediated deprotection of the N-allyloxycarbonyl amine using iodine in wet acetonitrile. The applicability of this transformation has been demonstrated by deprotecting a variety of N-allyloxycarbonyl amines, α-aminomethyl esters and simple N-allyloxycarbonyl alkyl amines. Deprotection occurs in high yield (82–93%) without erosion of the optical purity of the chiral substrates.

中文翻译:

温和的非过渡金属催化的N-烯丙氧羰基胺的脱保护

2S)-2-氨基-4-氧代2,4-二苯基丁酸甲酯的合成是通过在湿乙腈中使用碘的新型一锅式非过渡金属介导的N-烯丙氧羰基胺的脱保护作用而实现的。通过使各种N-烯丙氧基羰基胺,α-氨基甲基酯和简单的N-烯丙氧基羰基烷基胺脱保护,证明了该转化的适用性。脱保护以高收率(82-93%)进行,而不会影响手性底物的光学纯度。
更新日期:2017-01-31
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