Entry into Lithium Ynolates from α,α,α-Tribromomethyl Ketones: Synthesis of Cyclobutenes via the [2+2] Cycloaddition with α,β-Unsaturated Carbonyls

被引：2

作者：

Yamaoka, Yousuke ^{[1
,2
]}

Imahori, Hidetaka ^{[1
]}

Namioka, Motoki ^{[1
]}

Nishina, Ryo ^{[1
]}

Kobori, Yukiko ^{[1
]}

Ueda, Motoki ^{[1
]}

Shindo, Mitsuru ^{[3
]}

Takasu, Kiyosei ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Kyoto 6068501, Japan

[2] Hyogo Med Univ, Sch Pharm, Kobe 7708505, Japan

[3] Kyushu Univ, Inst Mat Chem & Engn, Kasuga, Fukuoka 8168580, Japan

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 09期

关键词：

DEMAND 1,3-DIPOLAR CYCLOADDITION; SILYL ENOL ETHERS; STEREOSELECTIVE-SYNTHESIS; HOMOGENEOUS HYDROGENATION; TETRASUBSTITUTED OLEFINS; ESTER HOMOLOGATION; ALPHA-BROMO; DERIVATIVES; IMINES; CARBANIONS;

D O I：

10.1021/acs.orglett.4c00202

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This study reports the synthesis of cyclobutene derivatives in good yields via the [2 + 2] cycloaddition between lithium ynolates and alpha,beta-unsaturated carbonyls. The ynolates are generated from alpha,alpha,alpha-tribromomethyl ketones and tert-butyl lithium via a simple and novel method, which does not produce any harmful byproducts, such as lithium alkoxide, which induces a polymerization reaction with alpha,beta-unsaturated carbonyls.

引用

页码：1896 / 1901

页数：6

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