2-ethynylaziridines as chiral carbon nucleophiles: stereoselective synthesis of 1,3-amino alcohols with three stereocenters via allenylindium reagents bearing a protected amino group.
2-ethynylaziridines as chiral carbon nucleophiles: stereoselective synthesis of 1,3-amino alcohols with three stereocenters via allenylindium reagents bearing a protected amino group.
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2-乙炔基氮丙啶作为手性碳亲核试剂：通过带有受保护氨基的联烯基试剂立体选择性合成具有三个立体中心的 1,3-氨基醇。
DOI：
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发表时间：
2001
影响因子：
3.6
通讯作者：
T. Tanaka
中科院分区：
文献类型：
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作者：
H. Ohno;H. Hamaguchi;T. Tanaka
在Pd（PPh（3））（4）和H（2）O存在下，由N-保护的3-烷基-2-乙炔基氮杂环丙烷与InI反应，有效地合成了带有保护氨基的联烯基铟试剂。丙二烯铟与脂肪族或芳香族醛的立体选择性加成反应可得到带有三个相邻手性中心的1，3-氨基醇，而2，3-反式-2-乙炔基氮杂环丙烷主要生成顺，顺式-2-乙炔基-1，3-氨基醇，而2，3-顺式氮杂环丙烷则选择性地生成反，顺式异构体。还描述了高度取代的乙炔基氮杂环丁烷的合成。
Allenylindium reagents bearing a protected amino group were effectively prepared from N-protected 3-alkyl-2-ethynylaziridines by treatment with InI in the presence of Pd(PPh(3))(4) and H(2)O. Stereoselective addition of the allenylindium to aliphatic or aromatic aldehydes affords 1,3-amino alcohols bearing three contiguous chiral centers: while 2,3-trans-2-ethynylaziridines yield syn,syn-2-ethynyl-1,3-amino alcohols predominantly, 2,3-cis-aziridines give anti,syn isomers selectively. Synthesis of highly substituted ethynylazetidines is also described.