Synthesis of Azepine Derivatives by Rhodium-Catalyzed Tandem 2,3-Rearrangement/Heterocyclization

被引：73

作者：

Nakamura, Itaru ^{[1
]}

Okamoto, Masashi ^{[2
]}

Sato, Yoshinori ^{[2
]}

Terada, Masahiro ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Res & Analyt Ctr Giant Mol, Sendai, Miyagi 9808578, Japan

[2] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 43期

关键词：

alkynes; nitrogen heterocycles; rearrangement; rhodium; ring expansion; INTERMOLECULAR 4+2 CYCLOADDITION; CYCLOPROPYL IMINES; 1ST; VINYLALLENE; VINYLCYCLOPROPANES; TRANSFORMATION; NITROGEN; ALKYNES;

D O I：

10.1002/anie.201205285

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Easy to N-cycle: The efficient synthesis of azepine derivatives was achieved by Rh-catalyzed tandem 2,3-rearrangement involving the heterocyclization of N-allenylnitrone intermediates (see scheme; cod=1,5-cyclooctadiene, tppms=sodium diphenylphosphinobenzene-3-sulfonate). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：10816 / 10819

页数：4

共 52 条

[11] RHODIUM(I)-CATALYZED INTRAMOLECULAR CARBOCYCLIC RING FUSION - A NEW APPROACH TO MEDIUM-SIZED-RING KETONES [J].

HUFFMAN, MA ;

LIEBESKIND, LS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (11) :4895-4896

[12] NICKEL(0)-CATALYZED SYNTHESIS OF SUBSTITUTED PHENOLS FROM CYCLOBUTENONES AND ALKYNES [J].

HUFFMAN, MA ;

LIEBESKIND, LS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (07) :2771-2772

[13]

Jeong N, 2005, MODERN RHODIUM-CATALYZED ORGANIC REACTIONS, P215, DOI 10.1002/3527604693.ch11

[14] Carbonylative [5+1] cycloaddition of cyclopropyl imines catalyzed by ruthenium carbonyl complex [J].

Kamitani, A ;

Chatani, N ;

Morimoto, T ;

Murai, S .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :9230-9233

[15]

Karibe Y., 2012, ANGEW CHEM, V124, P6318

[16] Chromium(0)-Catalyzed Tandem Cyclization of α,β-Unsaturated Thioimidates Containing an Enyne Moiety [J].

Karibe, Yusuke ;

Kusama, Hiroyuki ;

Iwasawa, Nobuharu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (25) :6214-6218

[17] In situ generation of vinyl allenes and its applications to one-pot assembly of cyclohexene, cyclooctadiene, 3,7-nonadienone, and bicyclo[6.4.0]dodecene derivatives with palladium-catalyzed multicomponent reactions [J].

Lee, PH ;

Lee, K ;

Kang, YJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) :1139-1146

[18] Rhodium-Catalyzed Carbonylation of 3-Acyloxy-1,4-enynes for the Synthesis of Cyclopentenones [J].

Li, Xiaoxun ;

Huang, Suyu ;

Schienebeck, Casi M. ;

Shu, Dongxu ;

Tang, Weiping .

ORGANIC LETTERS, 2012, 14 (06) :1584-1587

[19] Rhodium-Catalyzed Ring Expansion of Cyclopropanes to Seven-membered Rings by 1,5 C-C Bond Migration [J].

Li, Xiaoxun ;

Zhang, Min ;

Shu, Dongxu ;

Robichaux, Patrick J. ;

Huang, Suyu ;

Tang, Weiping .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (44) :10421-10424

[20] Azepine Synthesis from Alkyl Azide and Propargylic Ester via Gold Catalysis [J].

Liu, Heng ;

Li, Xin ;

Chen, Zili ;

Hu, Wen-Xiang .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (11) :5184-5190

← 1 2 3 4 5 6 →