Iron-catalyzed regio- and stereoselective substitution of 2,4-alkadienyl carboxylates with aryl Grignard reagents

被引：2

作者：

Miyanaka, Kento ^{[1
]}

Harada, Tomona ^{[1
]}

Shigeta, Masayuki ^{[1
]}

Hata, Takeshi ^{[1
,2
]}

Urabe, Hirokazu ^{[1
]}

机构：

[1] Tokyo Inst Technol, Sch Life Sci & Technol, 4259-B-59 Nagatsuta Cho,Midori Ku, Yokohama, Kanagawa 2268501, Japan

[2] Meiji Univ, Dept Appl Chem, 1-1-1 Higashimita,Tama Ku, Kawasaki, Kanagawa 2148571, Japan

来源：

TETRAHEDRON LETTERS | 2023年 / 133卷

关键词：

Iron catalyst; Grignard reagent; Dienyl carboxylate; S N 2 ' substitution; SELECTIVE CONJUGATE ADDITION; ALLYLIC ALKYLATION; METALATIVE CYCLIZATION; SALT-FREE; DERIVATIVES; ORGANOCOPPER; CARBONATES; CYCLOISOMERIZATION; REGIOCHEMISTRY; PHOSPHATES;

D O I：

10.1016/j.tetlet.2023.154824

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 2,4-alkadienyl carboxylates with an aryl Grignard reagent in the presence of a catalytic amount of FeCl2 affords diene derivatives in high yields with regio- and cis-stereoselectivity. Additionally, optically active 2,4-alkadienyl carboxylates afford the corresponding optically active dienes in high yields and with excellent degrees of chiral transfer. More importantly, the absolute structures of both starting material and product clarified the stereochemical pathway.

引用

页数：4

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