Design and synthesis of oxacycles from norbornene derivatives via ring-opening metathesis and ring-rearrangement metathesis

被引：10

作者：

Kotha, Sambasivarao ^{[1
]}

Ravikumar, Ongolu ^{[1
]}

Sreevani, Gaddamedi ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Powai, India

来源：

TETRAHEDRON | 2016年 / 72卷 / 42期

关键词：

Ring-rearrangement metathesis; Spirocycles; Oxacycles; Norbornene derivatives; DIELS-ALDER REACTION; DIVERSITY-ORIENTED APPROACH; ENYNE METATHESIS; RUTHENIUM; OXA; HETEROCYCLES; MECHANISM; LACTAM; BOWLS;

D O I：

10.1016/j.tet.2016.08.073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Norbornene derivatives containing oxygen atom(s) are found to undergo ring-rearrangement metathesis sequence to deliver cyclic ethers. Here, we have established a simple, efficient and an atom-economic process for the synthesis of fused and spiro-oxacyclic compounds starting with cyclopentadiene. Compounds prepared in this study are difficult to assemble by conventional retrosynthetic routes. (C) 2016 Published by Elsevier Ltd.

引用

页码：6611 / 6615

页数：5

共 50 条

[21] Ring-Opening Metathesis Polymerization of Coumarin-Containing Norbornene
Mikhail A Tlenkopatchev
Serguei Fomine
Lioudmila Fomina
Ruben Gaviño
Takeshi Ogawa
Polymer Journal, 1997, 29 : 622 - 625
[22] The synthesis and ring-opening metathesis polymerization of an amphiphilic redox-active norbornene
Watson, KJ
Nguyen, ST
Mirkin, CA
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 606 (01) : 79 - 83
[23] Synthesis and Ring-Opening Metathesis Polymerization of Norbornene-Terminated Syndiotactic Polypropylene
Anderson-Wile, Amelia M.
Coates, Geoffrey W.
Auriemma, Finizia
De Rosa, Claudio
Silvestre, Amelia
MACROMOLECULES, 2012, 45 (19) : 7863 - 7877
[24] Synthesis of Intricate Fused N-Heterocycles via Ring-Rearrangement Metathesis
Kotha, Sambasivarao
Gunta, Rama
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (16): : 8527 - 8535
[25] Ring opening metathesis polymerization of norbornene derivatives with polar groups
Madan, R
Anand, RC
Varma, IK
INDIAN JOURNAL OF CHEMICAL TECHNOLOGY, 1998, 5 (02) : 74 - 80
[26] Synthesis of dendronized polymers via ring-opening metathesis polymerization
Jung, Hwayoon
Week, Marcus
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
[27] Ring-opening metathesis oolymerization (ROMP) via electroorganic synthesis
Ogawa, Kelli
Goetz, Adam
Boydston, Andrew
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
[28] Design of Living Ring-Opening Alkyne Metathesis
Fischer, Felix R.
Nuckolls, Colin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) : 7257 - 7260
[29] Catalytic enantioselective total synthesis of (+)-dumetorine by ring-rearrangement metathesis
Rueckert, Anke
Deshmukh, Prashant H.
Blechert, Siegfried
TETRAHEDRON LETTERS, 2006, 47 (45) : 7977 - 7981
[30] Aromatic ring-opening metathesis
Valeriia Hutskalova
Christof Sparr
Nature, 2025, 638 (8051) : 697 - 703

← 1 2 3 4 5 →