Silver(I)-catalyzed hydroamination of (3S, 4R)-4-acetoxy-3-[(R)-1-tert- butyldimethylsiloxy)ethyl]azetidine-2-one derivatives for the synthesis of carbapenem skeleton

被引：2

作者：

Jang, Jinho ^{[1
]}

Zhang, Linlin ^{[1
]}

Kim, Hye Jung ^{[1
]}

Lee, Sung Ryoung ^{[1
]}

Kim, Sung Hoon ^{[1
]}

机构：

[1] Konkuk Univ, Dept Chem, 120 Neungdong Ro, Seoul 05029, South Korea

来源：

TETRAHEDRON LETTERS | 2022年 / 94卷

关键词：

Hydroamination; Carbapenems; Barbier-type reaction; Rearrangement of carbapenem; STEREOSELECTIVE-SYNTHESIS; INTRAMOLECULAR HYDROAMINATION; EFFICIENT SYNTHESIS; BETA-LACTAMS; CYCLIZATION; 3-ALKOXYCARBONYL-1-BETA-METHYLCARBAPENEM; AUXILIARIES; AMIDATION; ALKYNES;

D O I：

10.1016/j.tetlet.2022.153712

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

From (3S, 4R)-4-acetoxy-3-[(R)-1-tert-butyldimethylsiloxy)ethyl]azetidine-2-one (AOSA), a common precursor for the synthesis of b-lactam antibiotics, zinc-mediated Barbier-type reaction and subsequent silver(I)-catalyzed hydroamination were conducted to build the carbapenem skeleton bearing carboxylate ester at the C-3 position. Depending on catalysts used, a new type of rearrangement was observed. It was also affected by reaction time and the quantities of catalysts. (c) 2022 Elsevier Ltd. All rights reserved.

引用

页数：5

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