Diastereoselective synthesis of aziridines from (1R)-10-(N,N-dialkylsulfamoyl)isobornyl 2H-azirine-3-carboxylates
Diastereoselective synthesis of aziridines from (1R)-10-(N,N-dialkylsulfamoyl)isobornyl 2H-azirine-3-carboxylates
复制标题
DOI：
10.1039/b202321k
复制
发表时间：
2002-08-21
期刊：
影响因子：
--
通讯作者：
Gilchrist, TL
中科院分区：
文献类型：
--
作者：
Alvares, YSP;Alves, MJ;Gilchrist, TL
描述了手性吖丙啶1a与亲核试剂和二烯的反应。硫醇。杂芳族氮化合物和苯基溴化镁加成到氮杂环丙烷1a上，得到官能化的氮杂环丙烷2/3a-h。对产物3c和3g进行了X射线衍射分析。在大多数情况下观察到氮丙啶1a的两个面的非对映异构体分化，但只有苯硫酚产生其单一的非对映异构体（2a）。大多数非对映异构体的混合物通过干式快速色谱法分离。苄胺产生了原始氮杂环丙烷1a的二聚体，即化合物9。代表性的共轭二烯（环戊二烯.呋喃和开链二烯）加入到手性氮杂环丙烷1a中。仅观察到差的选择性。在环戊二烯与更大体积的氮杂环丙烷1b的环加成反应中，选择性没有显著提高。
Reaction of the chiral azirine 1a with nucleophiles and dienes is described. Thiols. heteroaromatic nitrogen compounds and phenylmagnesium bromide add to the azirine 1a to give functionalised aziridines 2/3a-h. X-Ray crystal structures foil the products 3c and 3g have been obtained. Diastereodifferentiation of the two faces of the azirine 1a is observed in most cases, but only thiophenol gibes it single diastereomer (2a). Most mixtures of diastereomers were separated by dry flash chromatography. Benzylamine produced a dimer of the original azirine 1a, compound 9. Representative conjugated dienes (cyclopentadiene. furan and open chain dienes) were added to the chiral azirine 1a. Only poor selectivities were observed. The selectivity as not significantly enhanced in the cycloaddition of cyclopentadiene to the more bulky azirine 1b.