Stereoselective Formation of cis-Trisubstituted 1,3-Dioxanes

被引：1

作者：

Hlokoane, Oriel ^{[1
,2
]}

Tsukamoto, Shuntaro ^{[1
]}

Irie, Raku ^{[1
]}

Oikawa, Masato ^{[1
]}

机构：

[1] Yokohama City Univ, Kanazawa Ku, 22-2 Seto, Yokohama, Kanagawa 2360027, Japan

[2] Natl Univ Lesotho, Dept Pharm, PO Roma 180, Maseru, Lesotho

来源：

CHEMISTRY LETTERS | 2021年 / 50卷 / 08期

关键词：

Oxa-Michael reaction; Prins reaction; cis-Trisubstituted 1,3-dioxane; AMINO-ACID; PRINS;

D O I：

10.1246/cl.210241

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein we report stereoselective formation of 1,3-dioxanes by oxa-Michael reaction of cis-arranged delta-siloxyenones using 1,3,5-trioxane and methanesulfonic acid (MsOH). The yields were satisfactory ranging from 81% to 95% (five examples). We furthermore studied the reaction of the ester analog with the same combination of reagents and found that stereoselective formation of tetrahydropyran by Prins reaction takes place in moderate yield of 68%. This methodology would be generally employed in the synthesis of cis-arranged heterocyclic systems which are otherwise not readily accessible.

引用

页码：1464 / 1466

页数：3

共 22 条

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