Superior Alkylating Agents for Bulky Esters/Ketones via Strontium-Mediated Barbier-Type Reaction

被引：7

作者：

Ohmura, Satoshi D. ^{[1
]}

Miyazaki, Yasuaki ^{[1
]}

Kanehiro, Daisuke ^{[1
]}

Yamaguchi, Yuka ^{[1
]}

Kitakata, Saki ^{[1
]}

Tateda, Sawa ^{[1
]}

Nishizawa, Takahiro ^{[1
]}

Shimoda, Ryosuke ^{[1
]}

Nagaoka, Gen ^{[1
]}

Ueno, Masaharu ^{[1
]}

Miyoshi, Norikazu ^{[1
]}

机构：

[1] Tokushima Univ, Dept Nat Sci, Grad Sch Technol Ind & Social Sci, Minami Josanjima 2-1, Tokushima 7708506, Japan

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 6卷 / 07期

关键词：

adamantanone; alkylation; Barbier-type reaction; ester; strontium; GRIGNARD-REAGENTS; ALKALINE-EARTH; COMPLEXES; CHEMISTRY; IMINES;

D O I：

10.1002/ajoc.201700209

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method has been developed for the Barbier-type alkylation reaction of bulky esters or ketones in the presence of metallic strontium and alkyl iodides. The reaction proceeded smoothly at ambient temperature to afford the fully alkylated corresponding alcohols in better yield than those obtained when using the corresponding Grignard reagents. The method is especially effective for introducing isobutyl or neopentyl groups into phenyl or adamantyl skeletons.

引用

页码：821 / 824

页数：4

共 29 条

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[23] Synthesis of 4-allenyl and 4-proparyl-2-azetidinone via Zn-mediated Barbier-type reaction and Pt-catalyzed intramolecular amidation to carbapenem skeletons
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[25] Chelation-controlled diastereoselective construction of N-aryl-, N-acyl/tosylhydrazono β-substituted aspartate derivatives via Barbier-type reaction
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[29] Samarium diiodide mediated barbier-type reaction of 2-chloromethylbenzoxazole and 2-chloromethylbenzothiazole with carbonyl compounds:: A convenient synthesis of 1-(β-hydroxyalkyl)benzoxazoles and 1-(β-hydroxyalkyl)benzothiazoles
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