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

共 50 条

[1] Iron-Catalyzed Regio- and Stereoselective Substitution of γ,δ-Epoxy-α,β-unsaturated Esters and Amides with Grignard Reagents
Hata, Takeshi
Bannai, Rie
Otsuki, Mamoru
Urabe, Hirokazu
ORGANIC LETTERS, 2010, 12 (05) : 1012 - 1014
[2] Iron-catalyzed highly regio- and stereoselective conjugate addition of 2,3-allenoates with Grignard reagents
Lu, Zhan
Chai, Guobi
Ma, Shengming
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (47) : 14546 - +
[3] Iron-Catalyzed Regio- and Stereoselective Conjugate Addition of Aryl-Grignard Reagents to α,β,γ,δ-Unsaturated Sulfones and its Synthetic Application
Hata, Takeshi
Nakada, Takuya
Oh, Yun Taek
Hirone, Naoki
Urabe, Hirokazu
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (09) : 1736 - 1740
[4] Iron-catalyzed regio- and stereoselective carbolithiation of alkynes
Hojo, M
Murakami, Y
Aihara, H
Sakuragi, R
Baba, Y
Hosomi, A
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (03) : 621 - 623
[5] Practical Iron-Catalyzed Allylations of Aryl Grignard Reagents
Mayer, Matthias
Czaplik, Waldemar M.
Jacobi von Wangelin, Axel
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (13) : 2147 - 2152
[6] Regio- and Stereospecific Copper-Catalyzed Substitution Reaction of Propargylic Ammonium Salts with Aryl Grignard Reagents
Guisan-Ceinos, Manuel
Martin-Heras, Victor
Tortosa, Mariola
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (25) : 8448 - 8451
[7] Iron-catalyzed regio- and stereoselective addition of acid chlorides to alkynes
Wang, Bo
Wang, Shihua
Li, Pinhua
Wang, Lei
CHEMICAL COMMUNICATIONS, 2010, 46 (32) : 5891 - 5893
[8] New General Method for Regio- and Stereoselective Allylic Substitution with Aryl and Alkenyl Coppers Derived from Grignard Reagents
Kiyotsuka, Yohei
Katayama, Yuji
Acharya, Hukurn P.
Hyodo, Tomonori
Kobayashi, Yuichi
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (05): : 1939 - 1951
[9] Iron-catalyzed coupling of aryl grignard reagents with alkyl halides
Hedstrom, Anna
Norrby, Per-Ola
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[10] Iron-catalyzed 1,6-addition of aryl Grignard reagents to 2,4-dienoates and -dienamides
Fukuhara, K
Urabe, H
TETRAHEDRON LETTERS, 2005, 46 (04) : 603 - 606

← 1 2 3 4 5 →