Synthesis of oxacyclic scaffolds via dual ruthenium hydride/Brønsted acid-catalyzed isomerization/cyclization of allylic ethers

A ruthenium hydride/Brønsted acid-catalyzed tandem sequence is reported for the synthesis of 1,3,4,9-tetrahydropyrano[3,4-b]indoles (THPIs) and related oxacyclic scaffolds. The process was designed on the premise that readily available allylic ethers would undergo sequential isomerization, first to...

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Main Authors: Hansen, Casper L., Ascic, Erhad, Ohm, Ragnhild G., Petersen, Rico, Hansen, Mette R., Madsen, Daniel, Tanner, David, Nielsen, Thomas E.
Other Authors: Singapore Centre for Environmental Life Sciences Engineering
Format: Article
Language:English
Published: 2014
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Online Access:https://hdl.handle.net/10356/103032
http://hdl.handle.net/10220/19161
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1030322020-03-07T12:47:11Z Synthesis of oxacyclic scaffolds via dual ruthenium hydride/Brønsted acid-catalyzed isomerization/cyclization of allylic ethers Hansen, Casper L. Ascic, Erhad Ohm, Ragnhild G. Petersen, Rico Hansen, Mette R. Madsen, Daniel Tanner, David Nielsen, Thomas E. Singapore Centre for Environmental Life Sciences Engineering DRNTU::Engineering::Environmental engineering A ruthenium hydride/Brønsted acid-catalyzed tandem sequence is reported for the synthesis of 1,3,4,9-tetrahydropyrano[3,4-b]indoles (THPIs) and related oxacyclic scaffolds. The process was designed on the premise that readily available allylic ethers would undergo sequential isomerization, first to enol ethers (Ru catalysis), then to oxocarbenium ions (Brønsted acid catalysis) amenable to endo cyclization with tethered nucleophiles. This methodology provides not only an attractive alternative to the traditional oxa-Pictet–Spengler reaction for the synthesis of THPIs, but also convenient access to THPI congeners and other important oxacycles such as acetals. 2014-04-07T06:36:12Z 2019-12-06T21:04:13Z 2014-04-07T06:36:12Z 2019-12-06T21:04:13Z 2014 2014 Journal Article Ascic, E., Ohm, R. G., Petersen, R., Hansen, M. R., Hansen, C. L., Madsen, D., et al. (2014). Synthesis of Oxacyclic Scaffolds via Dual Ruthenium Hydride/Brønsted Acid-Catalyzed Isomerization/Cyclization of Allylic Ethers. Chemistry - A European Journal, 20(12), 3297-3300. 0947-6539 https://hdl.handle.net/10356/103032 http://hdl.handle.net/10220/19161 10.1002/chem.201304270 en Chemistry - a European journal © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic DRNTU::Engineering::Environmental engineering
spellingShingle DRNTU::Engineering::Environmental engineering
Hansen, Casper L.
Ascic, Erhad
Ohm, Ragnhild G.
Petersen, Rico
Hansen, Mette R.
Madsen, Daniel
Tanner, David
Nielsen, Thomas E.
Synthesis of oxacyclic scaffolds via dual ruthenium hydride/Brønsted acid-catalyzed isomerization/cyclization of allylic ethers
description A ruthenium hydride/Brønsted acid-catalyzed tandem sequence is reported for the synthesis of 1,3,4,9-tetrahydropyrano[3,4-b]indoles (THPIs) and related oxacyclic scaffolds. The process was designed on the premise that readily available allylic ethers would undergo sequential isomerization, first to enol ethers (Ru catalysis), then to oxocarbenium ions (Brønsted acid catalysis) amenable to endo cyclization with tethered nucleophiles. This methodology provides not only an attractive alternative to the traditional oxa-Pictet–Spengler reaction for the synthesis of THPIs, but also convenient access to THPI congeners and other important oxacycles such as acetals.
author2 Singapore Centre for Environmental Life Sciences Engineering
author_facet Singapore Centre for Environmental Life Sciences Engineering
Hansen, Casper L.
Ascic, Erhad
Ohm, Ragnhild G.
Petersen, Rico
Hansen, Mette R.
Madsen, Daniel
Tanner, David
Nielsen, Thomas E.
format Article
author Hansen, Casper L.
Ascic, Erhad
Ohm, Ragnhild G.
Petersen, Rico
Hansen, Mette R.
Madsen, Daniel
Tanner, David
Nielsen, Thomas E.
author_sort Hansen, Casper L.
title Synthesis of oxacyclic scaffolds via dual ruthenium hydride/Brønsted acid-catalyzed isomerization/cyclization of allylic ethers
title_short Synthesis of oxacyclic scaffolds via dual ruthenium hydride/Brønsted acid-catalyzed isomerization/cyclization of allylic ethers
title_full Synthesis of oxacyclic scaffolds via dual ruthenium hydride/Brønsted acid-catalyzed isomerization/cyclization of allylic ethers
title_fullStr Synthesis of oxacyclic scaffolds via dual ruthenium hydride/Brønsted acid-catalyzed isomerization/cyclization of allylic ethers
title_full_unstemmed Synthesis of oxacyclic scaffolds via dual ruthenium hydride/Brønsted acid-catalyzed isomerization/cyclization of allylic ethers
title_sort synthesis of oxacyclic scaffolds via dual ruthenium hydride/brønsted acid-catalyzed isomerization/cyclization of allylic ethers
publishDate 2014
url https://hdl.handle.net/10356/103032
http://hdl.handle.net/10220/19161
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