Direct AlCl3-catalyzed transformation of benzyl THP ethers and allyl benzyl ethers

被引：3

作者：

Bui, Tien Tan ^{[1
,2
]}

Kim, Hee-Kwon ^{[1
,2
]}

机构：

[1] Chonbuk Natl Univ Med Sch & Hosp, Mol Imaging & Therapeut Med Res Ctr, Dept Nucl Med, Jeonju 54907, South Korea

[2] Chonbuk Natl Univ, Biomed Res Inst, Chonbuk Natl Univ Hosp, Res Inst Clin Med, Jeonju 54907, South Korea

来源：

SYNTHETIC COMMUNICATIONS | 2021年 / 51卷 / 03期

基金：

新加坡国家研究基金会;

关键词：

Allyl ethers; Aluminum(III) chloride; catalysts; DPM azides; THP ethers; AZIDES;

D O I：

10.1080/00397911.2020.1829644

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

THP and allyl groups are frequently used for the protection of alcohols. In this study, novel direct transformations of benzyl THP ethers and allyl benzyl ethers, protected forms of alcohols, are reported. TMSN(3)and AlCl(3)were employed as key azide reagent and catalyst to perform direct conversion of benzyl THP ethers and allyl benzyl ethers to azido compounds. In addition, direct nucleophile additions of carbon nucleophiles to benzyl THP ethers and allyl benzyl ethers were successfully accomplished in the presence of catalytic AlCl3. The results indicate that this novel method could be applied to various direct transformations of benzyl THP ethers and allyl benzyl ethers such as azidation, allylation, and alkynylation.

引用

页码：388 / 397

页数：10

共 26 条

[21] 1-Allyl- and 1-Benzyl-3-methyl-1,2,3-triazolium Salts via Tandem Click Transformations
Fletcher, James T.
Keeney, Matthew E.
Walz, Sara E.
SYNTHESIS-STUTTGART, 2010, (19): : 3339 - 3345
[22] Access to chiral homoallylic vicinal diols from carbonyl allylation of aldehydes with allyl ethers via palladium-catalyzed allylic C-H borylation
Tian-Ci Wang
Pu-Sheng Wang
Dian-Feng Chen
Liu-Zhu Gong
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[23] Access to chiral homoallylic vicinal diols from carbonyl allylation of aldehydes with allyl ethers via palladium-catalyzed allylic C-H borylation
Wang, Tian-Ci
Wang, Pu-Sheng
Chen, Dian-Feng
Gong, Liu-Zhu
SCIENCE CHINA-CHEMISTRY, 2022, 65 (02) : 298 - 303
[24] Novel nickel-catalyzed coupling reaction of allyl ethers with chlorosilanes, alkyl tosylates, or alkyl halides promoted hy vinyl-Grignard reagent leading to allylsilanes or alkenes
Terao, J
Watabe, H
Watanabe, H
Kambe, N
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) : 1674 - 1678
[25] Copper-Catalyzed Three-Component Reaction of Alkynes, TMSN3, and Ethers: Regiocontrollable Synthesis of N1- and N2-Oxyalkylated 1,2,3-Triazoles
Bao, Pengli
Yue, Huilan
Meng, Na
Zhao, Xiaohui
Li, Jiangsheng
Wei, Wei
ORGANIC LETTERS, 2019, 21 (18) : 7218 - 7222
[26] ALCOHOLYSIS OF HYDRIDESILANES TO GIVE SILYL ETHERS CATALYZED BY RHODACARBORANES CLOSO-3,3-(PH3P)2-3-H-3,1,2-RHC2B9H11 AND CLOSO-3,3-(ETA-2,ETA-3-C7H7CH2)-3,1,2-RHC2B9H11
ZAKHARKIN, LI
ZHIGAREVA, GG
BULLETIN OF THE RUSSIAN ACADEMY OF SCIENCES-DIVISION OF CHEMICAL SCIENCE, 1992, 41 (07): : 1284 - 1285

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