Highly diastereoselective epimerization:: Stereodivergent synthesis of α-hydroxy-β-amino isopentanoic acid

被引：6
|
作者：
Seo, Woo Duck
Curtis-Long, Marcus J.
Ryu, Young Bae
Lee, Jin Hwan
Yang, Min Suk
Lee, Woo Song
Park, Ki Hun
机构：
[1] Trout Beck, Driffield YO25 8NX, E Yorkshire, England
[2] Korea Res Inst Biosci & Biotechnol, Taejon 305333, South Korea
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 13期
关键词：
D O I：
10.1021/jo060309m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The high diastereoselectivity of the base-catalyzed epimerization of oxazolidin-2- ones 7 and 8 is shown to depend on the nature of the N-substituent (R group); when R = Bn, the 4,5-trans-product (4S,5R)-9 is formed, whereas when R = H the 4,5-cis-product (4S,5S)-10 is formed, both with > 99:1 dr. The successful hydrolysis of the oxazolidin-2-one group in both cis- and trans-derivatives show this to be a stereodivergent route to enantiopure alpha-hydroxy-beta-amino isopentanoic acids (2R,3S)-1 and (2S,3S)-2.
引用
收藏
页码：5008 / 5011
页数：4
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