One-pot enyne ring-closing metathesis-Diels-Alder reactions for the synthesis of polycyclic sulfamides

被引：7

作者：

Hill-Cousins, Joseph T. ^{[1
]}

Salim, Sofia S. ^{[1
]}

Bakar, Youssef M. ^{[1
]}

Bellingham, Richard K. ^{[2
]}

Light, Mark E. ^{[1
]}

Brown, Richard C. D. ^{[1
]}

机构：

[1] Univ Southampton, Dept Chem, Southampton SO17 1BJ, Hants, England

[2] GlaxoSmithKline, Dept Synthet Chem, Chem Dev, Tonbridge TN11 9AN, Kent, England

来源：

TETRAHEDRON | 2014年 / 70卷 / 23期

基金：

英国工程与自然科学研究理事会;

关键词：

Metathesis; Enyne; Sulfamide; Diels-Alder; One-pot; SOLID-PHASE SYNTHESIS; NATURAL-PRODUCTS; ACID; ISOMERIZATION; DERIVATIVES; STRATEGIES;

D O I：

10.1016/j.tet.2014.04.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ring-closing metathesis (RCM) and sequential Yb(OTf)(3) promoted Diels-Alder reactions of sulfamide-linked enynes proceeded selectively in one-pot-to afford-a series of bicyclic and tricyclic sulfamides. Excellent levels of diastereoselectivity are observed for the cycloaddition step, with only the endo-adducts being isolated. The protocol was further extended to incorporate a one-pot RCM-cross metathesis (CM)-Diels-Alder sequence, permitting rapid access to high levels of molecular complexity from simple and easily accessible precursors. Crown Copyright (C) 2014 Published by Elsevier Ltd. All rights reserved.

引用

页码：3700 / 3706

页数：7

共 50 条

[41] Entry into (E)-3-(1,2,4-oxadiazol-5-yl)acrylic acids via a one-pot ring-opening/ring-closing/retro-Diels-Alder reaction sequence
Presnukhina, Sofia
Tarasenko, Marina
Baykov, Sergey
Smirnov, Sergey N.
Boyarskiy, Vadim P.
Shetnev, Anton
Korsakov, Mikhail K.
TETRAHEDRON LETTERS, 2020, 61 (09)
[42] Imino Diels-Alder reactions:: an efficient one-pot synthesis of pyrano and furanoquinoline derivatives catalyzed by SbCl3
Maiti, Gourhari
Kundu, Pradip
TETRAHEDRON LETTERS, 2006, 47 (32) : 5733 - 5736
[43] A One-Pot Ring-Opening/Ring-Closure Sequence for the Synthesis of Polycyclic Spirooxindoles
Ren, Ji-Wei
Zhao, Qing-Lan
Xiao, Jun-An
Xia, Peng-Ju
Xiang, Hao-Yue
Chen, Xiao-Qing
Yang, Hua
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (18) : 4673 - 4677
[44] Dehydrogenation and Diels-Alder reactions in a one-pot synthesis of benzaldehyde from n-butane over acid catalysts
Sanchez-Garcia, Jose-Luis
Garcia-Alamilla, Ricardo
Martin Gonzalez-Chavez, Marco
Handy, Brent E.
Cardenas-Galindo, Maria-Guadalupe
CATALYSIS COMMUNICATIONS, 2012, 27 : 154 - 158
[45] 4-Picoline-catalyzed hetero-Diels-Alder type reactions: one-pot synthesis of pyrano[4,3-c]chromenes
Terzidis, Michael A.
Dimitriadou, Eleni
Tsoleridis, Constantinos A.
Stephanidou-Stephanatou, Julia
TETRAHEDRON LETTERS, 2009, 50 (19) : 2174 - 2176
[46] Design and synthesis of polycyclic sulfones via Diels-Alder reaction and ring-rearrangement metathesis as key steps
Kotha, Sambasivarao
Gunta, Rama
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 1373 - 1378
[47] Tandem aza-Claisen rearrangement and ring-closing metathesis reactions: the stereoselective synthesis of functionalised carbocyclic amides
Swift, Michael D.
Donaldson, Adele
Sutherland, Andrew
TETRAHEDRON LETTERS, 2009, 50 (26) : 3241 - 3244
[48] Synthesis of Four Illudalane Sesquiterpenes Utilizing a One-Pot Diels-Alder/Oxidative Aromatization Sequence
Xun, Miao-Miao
Bai, Yunli
Wang, Yanhong
Hu, Zhiyong
Fu, Kai
Ma, Wenbing
Yuan, Changchun
ORGANIC LETTERS, 2019, 21 (17) : 6879 - 6883
[49] One-Pot Three-Component Synthesis of Phenanthrenes via Palladium-Catalyzed Catellani and Retro-Diels-Alder Reactions
Hao, Tianxin
Gao, Wei
Yuan, Sitian
Liu, Yi
Li, Yiqing
Fu, Yang
Ding, Qiuping
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (15) : 10426 - 10433
[50] Efficient one-pot synthesis of novel and diverse tetrahydroquinolines bearing pyranopyrazoles using organocatalyzed domino Knoevenagel/hetero Diels-Alder reactions
Pandit, Rameshwar Prasad
Lee, Yong Rok
MOLECULAR DIVERSITY, 2014, 18 (01) : 39 - 50

← 1 2 3 4 5 →