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A flexible enantioselective approach to 3,4-dihydroxyprolinol derivatives by SmI2-mediated reductive coupling of chiral nitrone with ketones/aldehydes

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A flexible enantioselective approach to 3,4-dihydroxyprolinol derivatives by SmI2-mediated reductive coupling of chiral nitrone with ketonesaldehydes.htm (413bytes)
Date
2012-08-19
Author
Zhang, Hong-Kui
张洪奎
Xu, Shou-Qiang
Zhuang, Jia-Jia
Ye, Jian-Liang
Huang, Pei-Qiang
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  • 化学化工-已发表论文 [14469]
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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):6656-6664
URI
http://dx.doi.org/10.1016/j.tet.2012.06.006
WOS:000306618400003
https://dspace.xmu.edu.cn/handle/2288/14924

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