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

[21] Iron-Catalyzed Hydroborylative Cyclization of 1,6-Enynes
Cabrera-Lobera, Natalia
Rodriguez-Salamanca, Patricia
Nieto-Carmona, Juan C.
Bunuel, Elena
Cardenas, Diego J.
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (04) : 784 - 788
[22] Pd-catalyzed borylative cyclization of 1,6-enynes
Marco-Martinez, Juan
Lopez-Carrillo, Veronica
Bunuel, Elena
Simancas, Raquel
Cardenas, Diego J.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (07) : 1874 - +
[23] Electrophilic Cyclization of 1,6-Enynes
Harschneck, Tobias
Kirsch, Stefan F.
Wegener, Michael
SYNLETT, 2011, (08) : 1151 - 1153
[24] Directing effects of tethered alkenes in nickel-catalyzed coupling reactions of 1,6-enynes and aldehydes
Moslin, Ryan A.
Miller, Karen M.
Jamison, Timothy F.
TETRAHEDRON, 2006, 62 (32) : 7598 - 7610
[25] Synthesis and Rh-catalyzed reductive cyclization of 1,6-enynes and 1,6-diynes containing alkynylboronate termini
Pell, Christopher J.
Ozerov, Oleg, V
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2020, 912
[26] Rhodium-catalyzed asymmetric borylative cyclization of 1,6-enynes
Kinder, Robert E.
Widenhoefer, Ross A.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
[27] Rhodium-catalyzed asymmetric cyclization/hydroboration of 1,6-enynes
Kinder, RE
Widenhoefer, RA
ORGANIC LETTERS, 2006, 8 (10) : 1967 - 1969
[28] PALLADIUM-CATALYZED ALKYLATIVE CYCLIZATION OF 1,6-ENYNES AND 1,7-ENYNES
TROST, BM
PFRENGLE, W
URABE, H
DUMAS, J
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) : 1923 - 1924
[29] Iron-catalyzed reductive cyclization reaction of 1,6-enynes for the synthesis of 3-acylbenzofurans and thiophenes
Xia, Xiao-Feng
He, Wei
Zhang, Guo-Wei
Wang, Dawei
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (03) : 342 - 346
[30] Bismuth-catalyzed cyclization of amino-1,6-enynes
Komeyama, Kimihiro
Miyagi, Motoyoshi
Takaki, Ken
HETEROATOM CHEMISTRY, 2008, 19 (06) : 644 - 648

← 1 2 3 4 5 →