Nickel-catalyzed reductive cyclization of unactivated 1,6-enynes in the presence of organozinc reagents

被引：47

作者：

Chen, Mao ^{[1
]}

Weng, Yue ^{[1
]}

Guo, Mian ^{[1
]}

Zhang, Hua ^{[1
]}

Lei, Aiwen ^{[1
]}

机构：

[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 12期

关键词：

cyclization; enynes; nickel; organozinc reagents; synthetic methods;

D O I：

10.1002/anie.200704452

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Pyrrolidine and tetrahydrofuran derivatives were synthesized in a highly stereoselective manner through the Ni-catalyzed reduction of the title compounds under mild conditions (see scheme). The product of cyclization is initially associated with both a Ni and a Zn species, the removal of which by elimination and hydrolysis corresponds to the formal incorporation of dihydrogen. acac=acetylacetonate; R=alkyl, aryl; X=N, O. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2279 / 2282

页数：4

共 50 条

[41] Cyclization of 1,6-enynes with allylic chromate species
Nishikawa, T
Shinokubo, H
Oshima, K
ORGANIC LETTERS, 2002, 4 (16) : 2795 - 2797
[42] Palladium-catalyzed enantioselective cyclization of silyloxy-1,6-enynes
Corkey, Britton K.
Toste, F. Dean
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (10) : 2764 - +
[43] Rh-Catalyzed Borylative Cyclization of Acrylate-Containing 1,6-Enynes
Yang, Zhantao
Yu, Zhiqiang
He, Yulin
Feng, Wei
Zhang, Yinchao
Wang, Junjie
Kong, Xiangtao
Yang, Chun-Hua
ORGANIC LETTERS, 2023, 25 (30) : 5671 - 5675
[44] Cationic Pd(II)-catalyzed arylative cyclization of 1,6-enynes with arylboronic acids
Shen, Kun
Han, Xiuling
Lu, Xiyan
Hu, Zhiyong
TETRAHEDRON LETTERS, 2017, 58 (39) : 3768 - 3771
[45] Rhodium-catalyzed cyclization of 1,6-enynes triggered by addition of arylboronic acids
Miura, T
Shimada, M
Murakami, M
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (04) : 1094 - 1095
[46] Palladium-Catalyzed Enantioselective Cyclization of 1,6-Enynes to Access Chiral γ-Butyrolactam
Zhang, Liren
Wang, Yuanfang
Tang, Junlong
Wu, Wanqing
Jiang, Huanfeng
JOURNAL OF ORGANIC CHEMISTRY, 2024, 90 (01): : 894 - 898
[47] Ruthenium-Catalyzed Hydroalkynylative Cyclization of 1,6-Enynes Induced by Substituent Effects
Liu, Rui
Ni, Zhenjie
Giordano, Laurent
Tenaglia, Alphonse
ORGANIC LETTERS, 2016, 18 (16) : 4040 - 4043
[48] Chiral carbene approach to gold-catalyzed asymmetric cyclization of 1,6-enynes
Matsumoto, Yasumasa
Selim, Khalid B.
Nakanishi, Hirotsugu
Yamada, Ken-ichi
Yamamoto, Yasutomo
Tomioka, Kiyoshi
TETRAHEDRON LETTERS, 2010, 51 (02) : 404 - 406
[49] RHODIUM (1) CATALYZED REGIOSPECIFIC CYCLIZATION OF 1,6-ENYNES TO METHYLENECYCLOHEX-2-ENES
GRIGG, R
STEVENSON, P
WORAKUN, T
TETRAHEDRON, 1988, 44 (15) : 4967 - 4972
[50] Merging Hydrogen Atom Transfer and Halogen Atom Transfer forIodide-Catalyzed Radical Reductive Cyclization of 1,6-Enynes
Ding, Linglong
Deng, Yi-Hui
Sun, Tian-Yu
Jiang, Yuqin
Xia, Xiao-Feng
ORGANIC LETTERS, 2022, 24 (17) : 3113 - 3117

← 1 2 3 4 5 →