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Synlett 2015; 26(10): 1305-1339
DOI: 10.1055/s-0034-1380402
DOI: 10.1055/s-0034-1380402
account
Harnessing the Versatile Reactivity of Propargyl Alcohols and their Derivatives for Sustainable Complex Molecule Synthesis
Further Information
Publication History
Received: 18 November 2014
Accepted after revision: 27 January 2015
Publication Date:
15 April 2015 (online)
Abstract
One of the major challenges faced in modern synthetic chemistry is the efficient and selective assembly of complex molecular structures, especially carbo- and heterocycles, from readily accessible starting materials. With this has arisen the development of tandem reaction processes, which permit multiple transformations in a single synthetic step and that have often provided elegant routes to complex target scaffolds from simple precursors. Propargyl alcohols and their derivatives have become increasingly attractive starting materials for such processes owing to their reactivity in the presence of a Brønsted or Lewis acid catalyst as well as halogenation reagents. This account describes our recent efforts in the field, and demonstrates how propargyl alcohols and their derivatives can be transformed into a diverse range of highly functionalized acyclic, carbocyclic and heterocyclic structures, which are of importance as synthetic building blocks and as motifs in functional materials and bioactive compounds.
1 Introduction
2 Acyclic Conjugated Enynes
3 Carbocycles
3.1 Indenes
3.2 Dihydrofluorenes
3.3 Cyclopentenes, Cyclobutenes and Cyclopenta[b]naphthalenes
3.4 ortho-Phenolic Esters
4 Heterocycles with One Heteroatom
4.1 Indoles
4.2 Piperidines, Azepines and Pyrrolidines
4.3 Pyrroles
4.4 Furans
4.5 Benzo[b]oxepines and Benzo[b]azepines
5 Heterocycles with Two Heteroatoms
5.1 Thiazoles and Oxazoles
5.2 Dioxolanes
6 Conclusion
-
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For selected reviews of tandem synthetic processes, see:
For selected reviews concerning the reactivity of unsaturated substrates and transition metal complexes, see:
For selected reviews concerning the reactions of propargyl alcohols and derivatives in the presence of gold catalysts, see refs 2e,f,i,k,m,n,p, and:
For selected reviews concerning the reactions of propargyl alcohols and derivatives in the presence of silver catalysts, see refs 2e,k,n,p, and:
For selected reviews, see:
For selected reviews, see:
For recent selected examples concerning indene synthesis, see:
For selected examples, see:
For selected examples of gold-catalyzed 1,n-enyne ester migrations, see:
For selected examples of gold-catalyzed 1,n-diyne ester migrations, see:
For recent selected examples concerning dihydrofluorene synthesis, see:
To our knowledge, only two prior reports have been described, see:
For recent selected examples concerning cyclopenta[b]naphthalenes, see:
For recent selected examples concerning bicyclo[3.2.0]hepta-1,5-dienes, see:
For recent selected examples, see:
For selected reviews, see:
For recent selected examples concerning indoles, see:
For illustrative examples, see:
For selected recent examples, see:
See ref. 16q, and:
For recent selected reviews on 2- and 3-oxindole synthesis, see:
For selected reviews on haloamination of unsaturated bonds, see:
For selected examples concerning azabicyclo[4.2.0]oct-5-enes, see:
For selected examples concerning azabicyclo[4.2.0]octa-1(8),5-dienes, see:
For recent examples illustrating pyrrole synthesis, see:
For selected reviews concerning furan motifs, see:
For selected examples illustrating furan synthesis, see:
For selected examples, see:
For recent selected examples, see:
For selected examples, see:
For recent selected examples, see:
For selected reviews, see: