Asymmetric synthesis of β2,3-amino acids by InI-Pd(0)-promoted metalation and addition of chiral 2-vinylaziridines
Asymmetric synthesis of β2,3-amino acids by InI-Pd(0)-promoted metalation and addition of chiral 2-vinylaziridines
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DOI：
10.1016/s0040-4020(02)00499-4
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发表时间：
2002-06-24
期刊：
影响因子：
2.1
通讯作者：
Takemoto, Y
中科院分区：
文献类型：
--
作者：
Anzai, M;Yanada, R;Takemoto, Y
光学活性的3-烷基-2-乙烯基氮杂环丙烷在碘化铟和钯（PPh_3）存在下与各种醛反应（4），立体选择性地生成具有三个相邻手性中心的顺式，顺式-2-乙烯基-1，3-氨基醇。顺式、顺式异构体与其他三种异构体的比例受氮丙啶的C3-取代基以及醛的烷基基团的显著影响。此外，所获得的1，3-氨基醇可以转化为生物学上重要的p（2，3）-氨基酸衍生物。(C)2002爱思唯尔科技有限公司版权所有。
The reaction of optically active 3-alkyl-2-vinylaziridines with various aldehydes in the presence of InI and Pd(PPh3)(4) gives rise to chiral syn,syn-2-vinyl-1,3-amino alcohols possessing three contiguous chiral centers stereoselectively. The ratio of the syn,syn-isomer to the other three isomers is significantly affected by the C3-substituents of aziridines as well as the alkyl groups of aldehydes. In addition, the obtained 1,3-aminoalcohols can be converted into biologically important p(2,3)-amino acid derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.