Stereodivergent total asymmetric synthesis of polyhydroxylated pyrrolidines via tandem allylic epoxidation and intramolecular cyclization reactions
Stereodivergent total asymmetric synthesis of polyhydroxylated pyrrolidines via tandem allylic epoxidation and intramolecular cyclization reactions
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DOI：
10.1016/j.tetlet.2004.06.048
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发表时间：
2004-08-09
影响因子：
1.8
通讯作者：
Han, H
中科院分区：
文献类型：
--
作者：
Singh, S;Han, H
用VO(acac)(2)/t-BuOOH体系对烯丙醇10和11进行环氧化，然后在分子内对得到的8-环氧氨基甲酸酯12、13、18和19进行5-外环化，为不对称合成多羟基吡咯烷提供了一种普遍而有效的解决方案。在所设计的非手性烯烃6的不对称氨基羟基化反应中，必需的邻氨基醇官能团被对映体/区域选择性地安装。(C) 2004 Elsevier Ltd.版权所有。
Epoxidation of the allylic alcohols 10 and 11 using the VO(acac)(2)/t-BuOOH system followed by an intramolecular 5-exo cyclization of the resulting 8-epoxycarbamates 12, 13, 18, and 19 has been shown to provide a general and efficient solution for the asymmetric synthesis of polyhydroxy pyrrolidines. The requisite vicinal amino alcohol functionality was enantio-/regio-selectively installed by the Os-catalyzed asymmetric aminohydroxylation reaction of the designed achiral olefin 6. (C) 2004 Elsevier Ltd. All rights reserved.