Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen


IMPACT FACTOR 2018: 2.350
5-year IMPACT FACTOR: 4.037

CiteScore 2018: 4.66

SCImago Journal Rank (SJR) 2018: 1.240
Source Normalized Impact per Paper (SNIP) 2018: 1.826

Online
ISSN
1365-3075
See all formats and pricing
More options …
Volume 78, Issue 2

Issues

Synthesis of spiroketals by iridium-catalyzed double hydroalkoxylation

Barbara A. Messerle
  • Corresponding author
  • School of Chemistry, University of New South Wales, Kensington, NSW 2052, Australia
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Khuong Q. Vuong
  • Corresponding author
  • School of Chemistry, University of New South Wales, Kensington, NSW 2052, Australia
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2009-01-01 | DOI: https://doi.org/10.1351/pac200678020385

A highly efficient approach to the synthesis of spiroketals involves the double cyclization of alkynyl diols using transition-metal catalysts. The iridium complex [Ir(PyP)(CO)2]BPh4 where PyP = 1-[(2-diphenylphosphino)ethyl]pyrazole is an effective catalyst for promoting the formation of spiroketals via this double hydroalkoxylation reaction. The complex promotes the formation of a series of spiroketal products from alkynyl diol starting materials such as 3-ethynylpentane-1,5-diol and 2-(4-hydroxybut-1-ynyl)benzyl alcohol. Stereoselective cyclization occurs for 3-ethynylpentane-1,5-diol, 3-ethynylhexane-1,6-diol. The cycloadditions occur in all but one case with quantitative conversion in under 24 h at 120 °C.

Keywords: alkyne diols; catalysis; hydroalkoxylation; spiroketals; transition metals

Conference

IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-13), International Symposium on Organometallic Chemistry Directed Toward Organic Synthesis, OMCOS, Organometallic Chemistry Directed Toward Organic Synthesis, 13th, Geneva, Switzerland, 2005-07-17–2005-07-21

About the article

Published Online: 2009-01-01

Published in Print: 2006-01-01


Citation Information: Pure and Applied Chemistry, Volume 78, Issue 2, Pages 385–390, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/pac200678020385.

Export Citation

© 2013 Walter de Gruyter GmbH, Berlin/Boston.Get Permission

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[1]
Rachel M. Gillard and Margaret A. Brimble
Organic & Biomolecular Chemistry, 2019
[2]
Sami F Tlais and Gregory B Dudley
Beilstein Journal of Organic Chemistry, 2011, Volume 7, Page 570
[3]
Jiuyi Li, Hui Peng, Furong Wang, Xiujun Wang, Huanfeng Jiang, and Biaolin Yin
Organic Letters, 2016, Volume 18, Number 13, Page 3226
[4]
Vera Diachenko, Michael J. Page, Mark R. D. Gatus, Mohan Bhadbhade, and Barbara A. Messerle
Organometallics, 2015, Volume 34, Number 18, Page 4543
[5]
Ganesh Kumar Thota, Chandrahas Tarigopula, and Rengarajan Balamurugan
Tetrahedron, 2015, Volume 71, Number 15, Page 2280
[6]
Paulo H. S. Paioti, John M. Ketcham, and Aaron Aponick
Organic Letters, 2014, Volume 16, Number 20, Page 5320
[8]
Chandrababu Naidu Kona and C.V. Ramana
Tetrahedron, 2014, Volume 70, Number 23, Page 3653
[9]
Sophie Borghèse, Pauline Drouhin, Valérie Bénéteau, Benoit Louis, and Patrick Pale
Green Chemistry, 2013, Volume 15, Number 6, Page 1496
[11]
Shyamsundar Das, Boddeti Induvadana, and C.V. Ramana
Tetrahedron, 2013, Volume 69, Number 7, Page 1881
[13]
Stanisław Krompiec, Mateusz Penkala, Krzysztof Szczubiałka, and Ewelina Kowalska
Coordination Chemistry Reviews, 2012, Volume 256, Number 17-18, Page 2057
[14]
Igor Larrosa, Pedro Romea, and Fèlix Urpí
Tetrahedron, 2008, Volume 64, Number 12, Page 2683
[15]
C.V. Ramana, Boddeti Induvadana, Burgula Srinivas, Kommagalla Yadagiri, Madhusudhan N. Deshmukh, and Rajesh G. Gonnade
Tetrahedron, 2009, Volume 65, Number 47, Page 9819
[16]
Jaideep Saha, Chris Lorenc, Bikash Surana, and Mark W. Peczuh
The Journal of Organic Chemistry, 2012, Volume 77, Number 8, Page 3846
[18]
Selvasothi Selvaratnam, Joanne H.H. Ho, Paul B. Huleatt, Barbara A. Messerle, and Christina L.L. Chai
Tetrahedron Letters, 2009, Volume 50, Number 10, Page 1125
[19]
Kimihiro Komeyama, Takayuki Morimoto, Yuushou Nakayama, and Ken Takaki
Tetrahedron Letters, 2007, Volume 48, Number 18, Page 3259
[20]
Sophie R. Beeren, Serin L. Dabb, and Barbara A. Messerle
Journal of Organometallic Chemistry, 2009, Volume 694, Number 2, Page 309
[21]
Esther Delgado, Elisa Hernández, Ángel Nievas, Avelino Martín, and María José Recio
Journal of Organometallic Chemistry, 2010, Volume 695, Number 3, Page 446
[22]
Bradley Y.-W. Man, Mohan Bhadbhade, and Barbara A. Messerle
New Journal of Chemistry, 2011, Volume 35, Number 8, Page 1730
[23]
SungYong Seo and Tobin J. Marks
Chemistry - A European Journal, 2010, Volume 16, Number 17, Page 5148
[24]
Leslie D. Field, Barbara A. Messerle, Khuong Q. Vuong, and Peter Turner
Dalton Transactions, 2009, Number 18, Page 3599
[25]
Barbara A. Messerle and Khuong Q. Vuong
ChemInform, 2006, Volume 37, Number 31

Comments (0)

Please log in or register to comment.
Log in