A flexible enantioselective approach to 3,4-dihydroxyprolinol derivatives by SmI2-mediated reductive coupling of chiral nitrone with ketones/aldehydes
Date
2012-08-19Author
Zhang, Hong-Kui
张洪奎
Xu, Shou-Qiang
Zhuang, Jia-Jia
Ye, Jian-Liang
Huang, Pei-Qiang
Collections
- 化学化工-已发表论文 [14469]
Abstract
A flexible enantioselective approach to polyhydroxylated prolinol derivatives was described, which is based on the samarium diiodide-mediated reductive coupling of the chiral nitrone (3S,4R)-8, derived from D-isoascorbic acid with aldehydes/ketones. Thereby, polyhydroxyprolinol derivatives 9a-e and 9h-j were obtained from aromatic ketones and aliphatic aldehydes in good to excellent yields of 65-91%. These reductive hydroxyalkylations are highly diastereoselective in establishing the C-4 stereogenic center. By this way, the asymmetric syntheses of (-)-8a-epi-swainsonine (4) and (-)-8,8a-di-epi-swainsonine (5) have been achieved. (c) 2012 Elsevier Ltd. All rights reserved.
Citation
TETRAHEDRON,2012,68(33):6656-6664URI
http://dx.doi.org/10.1016/j.tet.2012.06.006WOS:000306618400003
https://dspace.xmu.edu.cn/handle/2288/14924