Neighboring Effect of Intramolecular Chlorine Atoms on Epoxide Opening Reaction by Chloride Anions

被引：8
|
作者：
Umezawa, Taiki [1 ]
Shibata, Masayuki [1 ]
Tamagawa, Ryutaro [1 ]
Matsuda, Fuyuhiko [1 ]
机构：
[1] Hokkaido Univ, Grad Sch Environm Sci, Div Environm Mat Sci, Sapporo, Hokkaido 0600810, Japan
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 19期
基金：
日本学术振兴会;
关键词：
OCHROMONAS-DANICA; POTERIOOCHROMONAS-MALHAMENSIS; ABSOLUTE-CONFIGURATION; CHLOROSULFOLIPIDS; BIOSYNTHESIS; DICHLORINATION; TOXICITY; STEREOCHEMISTRY; MYTILIPIN; REVISION;
D O I：
10.1021/acs.orglett.9b02624
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We investigated the diastereoselectivity of ring openings for chloro vinyl epoxides with various chlorination reagents. In the chlorinolysis reactions using vinyl epoxides having an allyl alcohol, inversion:retention ratios varied depending on the chloride sources. In limited cases, the increase in retention ratio was consistent with the intervention of chloronium ions. In contrast, all vinyl epoxides bearing an alpha,beta-unsaturated ester gave only the inversion products. These results suggest the electron-withdrawing property suppressed the chloronium ions.
引用
收藏
页码：7731 / 7735
页数：5
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