Literature DB >> 17940591

The Domino Way to Heterocycles.

Albert Padwa1, Scott K Bur.   

Abstract

Sequential transformations enable the facile synthesis of complex target molecules from simple building blocks in a single preparative step. Their value is amplified if they also create multiple stereogenic centers. In the ongoing search for new domino processes, emphasis is usually placed on sequential reactions which occur cleanly and without forming by-products. As a prerequisite for an ideally proceeding one-pot sequential transformation, the reactivity pattern of all participating components has to be such that each building block gets involved in a reaction only when it is supposed to do so. The development of sequences that combine transformations of fundamentally different mechanisms broadens the scope of such procedures in synthetic chemistry. This mini review contains a representative sampling from the last 15 years on the kinds of reactions that have been sequenced into cascades to produce heterocyclic molecules.

Year:  2007        PMID: 17940591      PMCID: PMC2031872          DOI: 10.1016/j.tet.2007.03.158

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  48 in total

1.  Introduction: Frontiers in Organic Synthesis.

Authors:  Paul A. Wender
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  Regioselective synthesis of the bridged tricyclic core of Garcinia natural products via intramolecular aryl acrylate cycloadditions.

Authors:  Eric J Tisdale; Chinmay Chowdhury; Binh G Vong; Hongmei Li; Emmanuel A Theodorakis
Journal:  Org Lett       Date:  2002-03-21       Impact factor: 6.005

3.  Substrate-Controlled Stereodifferentiation of Tandem [4 + 2]/[3 + 2] Cycloadditions by a Vicinal Carbohydrate-Based Template.

Authors:  Martin Avalos; Reyes Babiano; Pedro Cintas; Francisco J. Higes; José L. Jiménez; Juan C. Palacios; María A. Silva
Journal:  J Org Chem       Date:  1996-03-08       Impact factor: 4.354

4.  Total synthesis of (+)-dihydrocuscohygrine and cuscohygrine.

Authors:  Christian Stapper; Siegfried Blechert
Journal:  J Org Chem       Date:  2002-09-06       Impact factor: 4.354

5.  A Facile and Efficient Synthesis of Thieno[2,3-c]furans and Furo[3,4-b]indoles via a Pummerer-Induced Cyclization Reaction.

Authors:  C. Oliver Kappe; Albert Padwa
Journal:  J Org Chem       Date:  1996-09-06       Impact factor: 4.354

6.  Tandem double intramolecular [4 + 2]/[3 + 2] cycloadditions of nitroalkenes.

Authors:  S E Denmark; L Gomez
Journal:  Org Lett       Date:  2001-09-06       Impact factor: 6.005

7.  A novel sequential aminodiene Diels-Alder strategy for the rapid construction of substituted analogues of Kornfeld's ketone.

Authors:  Scott K Bur; Albert Padwa
Journal:  Org Lett       Date:  2002-11-14       Impact factor: 6.005

8.  Synthesis of diversely functionalized hexahydropyrrolo[2,3-b]indoles using domino reactions, olefination, isomerization and Claisen rearrangement followed by reductive cyclization.

Authors:  Tomomi Kawasaki; Atsuyo Ogawa; Romi Terashima; Toshiko Saheki; Naoko Ban; Hiroko Sekiguchi; Ken-ei Sakaguchi; Masanori Sakamoto
Journal:  J Org Chem       Date:  2005-04-15       Impact factor: 4.354

9.  Synthesis of Substituted 2-Pyridones via the Pummerer Cyclization-Deprotonation-Cycloaddition Cascade of Imidosulfoxides.

Authors:  Albert Padwa; Todd M. Heidelbaugh; Jeffrey T. Kuethe
Journal:  J Org Chem       Date:  1999-03-19       Impact factor: 4.354

10.  Tandem polar/radical crossover sequences for the formation of fused and bridged bicyclic nitrogen heterocycles involving radical ionic chain reactions, and alkene radical cation intermediates, performed under reducing conditions: scope and limitations.

Authors:  David Crich; Krishnakumar Ranganathan; Santhosh Neelamkavil; Xianhai Huang
Journal:  J Am Chem Soc       Date:  2003-07-02       Impact factor: 15.419

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  29 in total

1.  Novel and efficient one-pot five- and six-component reactions for the stereoselective synthesis of highly functionalized enaminones and dithiocarbamates.

Authors:  Morteza Bararjanian; Saeed Balalaie; Frank Rominger; Barahman Movassagh; Hamid Reza Bijanzadeh
Journal:  Mol Divers       Date:  2010-11-12       Impact factor: 2.943

2.  Four-component domino reaction providing an easy access to multifunctionalized tricyclo[6.2.2.0(1,6)]dodecane derivatives.

Authors:  Bo Jiang; Chao Li; Feng Shi; Shu-Jiang Tu; Parminder Kaur; Walter Wever; Guigen Li
Journal:  J Org Chem       Date:  2010-05-07       Impact factor: 4.354

3.  Efficient domino approaches to multifunctionalized fused pyrroles and dibenzo[b,e][1,4]diazepin-1-ones.

Authors:  Bo Jiang; Qiu-Yun Li; Hao Zhang; Shu-Jiang Tu; Suresh Pindi; Guigen Li
Journal:  Org Lett       Date:  2012-01-19       Impact factor: 6.005

4.  Dimethyl 11,13-dimethyl-16-[1,2-bis-(methoxy-carbon-yl)ethen-yl]-12-oxo-16,17-dioxa-18-aza-hexa-cyclo-[7.5.1.1.1.1.0]octa-deca-2,7-diene-2,3-dicarboxyl-ate.

Authors:  Atash V Gurbanov; Eugeniya V Nikitina; Elena A Sorokina; Fedor I Zubkov; Victor N Khrustalev
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-11-28

5.  Oppolzer-type intramolecular Diels-Alder cycloadditions via isomerizations of allenamides.

Authors:  John B Feltenberger; Richard P Hsung
Journal:  Org Lett       Date:  2011-05-25       Impact factor: 6.005

6.  A multi-component domino reaction for the direct access to polyfunctionalized indoles via intermolecular allylic esterification and indolation.

Authors:  Bo Jiang; Mian-Shuai Yi; Feng Shi; Shu-Jiang Tu; Suresh Pindi; Patrick McDowell; Guigen Li
Journal:  Chem Commun (Camb)       Date:  2011-10-31       Impact factor: 6.222

7.  Controlling Selectivity for Cycloadditions of Nitrones and Alkenes Tethered by Benzimidazoles: Combining Experiment and Theory.

Authors:  Liping Meng; Selina C Wang; James C Fettinger; Mark J Kurth; Dean J Tantillo
Journal:  European J Org Chem       Date:  2009-04

8.  An aza-Prins cyclization approach to functionalized indolizidines from 2-allylpyrrolidines.

Authors:  Xiaoxi Liu; Michael P McCormack; Stephen P Waters
Journal:  Org Lett       Date:  2012-10-25       Impact factor: 6.005

9.  Origin of stereocontrol in the construction of the 12-oxatricyclo[6.3.1.0(2,7)]dodecane ring system by Prins-pinacol reactions.

Authors:  Larry E Overman; Paul S Tanis
Journal:  J Org Chem       Date:  2010-01-15       Impact factor: 4.354

10.  Domino Heck-Aza-Michael Reactions: A One-Pot, Sequential Three-Component Approach to 1,1-Dioxido-1,2-benzisothiazoline-3-acetic Acid.

Authors:  Alan Rolfe; Kyle Young; Paul R Hanson
Journal:  European J Org Chem       Date:  2008
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