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The Synthesis of Hydrobenzoin-Based Monoaza Crown Ethers and Their Application as Recyclable Enantioselective Catalysts
New recyclable monoaza-15-crown ethers have been synthesized starting from ( R , R )-(+)- and ( S , S )-(−)-hydrobenzoin. These macrocycles proved to be efficient and reusable phase transfer catalysts in a few asymmetric reactions under mild conditions. The asymmetric epoxidation of trans -chalcone...
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| Published in: | Catalysis letters 2020-04, Vol.150 (4), p.930-938 |
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| Main Authors: | , , , , , |
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| cites | cdi_FETCH-LOGICAL-c473t-1bcb968a29901f100c266818fcda2433a99d770168e07b6a1776b6b55bd0e18f3 |
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| creator | Nemcsok, Tamás Rapi, Zsolt Bagi, Péter Oláh, Attila Keglevich, György Bakó, Péter |
| description | New recyclable monoaza-15-crown ethers have been synthesized starting from (
R
,
R
)-(+)- and (
S
,
S
)-(−)-hydrobenzoin. These macrocycles proved to be efficient and reusable phase transfer catalysts in a few asymmetric reactions under mild conditions. The asymmetric epoxidation of
trans
-chalcone took place with up to 81% ee, while using other chalcone derivatives, the products were formed with 68–88% ee. The hydrobenzoin-based lariat ethers were also tested in the cyclopropanation of a few electron deficient olefins using diethyl bromomalonate to afford the product with good enantioselectivities (54–75% ee). The catalysts were recovered by salt formation, followed by extraction, and were reused without the loss of the activity and effect on the enantioselectivity.
Graphic Abstract
The synthesis of hydrobenzoin-based monaza crown ethers and their application as recyclable enantioselective catalysts. |
| doi_str_mv | 10.1007/s10562-019-03013-0 |
| format | article |
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R
,
R
)-(+)- and (
S
,
S
)-(−)-hydrobenzoin. These macrocycles proved to be efficient and reusable phase transfer catalysts in a few asymmetric reactions under mild conditions. The asymmetric epoxidation of
trans
-chalcone took place with up to 81% ee, while using other chalcone derivatives, the products were formed with 68–88% ee. The hydrobenzoin-based lariat ethers were also tested in the cyclopropanation of a few electron deficient olefins using diethyl bromomalonate to afford the product with good enantioselectivities (54–75% ee). The catalysts were recovered by salt formation, followed by extraction, and were reused without the loss of the activity and effect on the enantioselectivity.
Graphic Abstract
The synthesis of hydrobenzoin-based monaza crown ethers and their application as recyclable enantioselective catalysts.</description><identifier>ISSN: 1011-372X</identifier><identifier>EISSN: 1572-879X</identifier><identifier>DOI: 10.1007/s10562-019-03013-0</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Alkenes ; Asymmetry ; Catalysis ; Catalysts ; Chemistry ; Chemistry and Materials Science ; Crown ethers ; Cyclopropane compounds ; Enantiomers ; Epoxidation ; Ethers ; Industrial Chemistry/Chemical Engineering ; Olefins ; Organometallic Chemistry ; Phase transfer catalysts ; Physical Chemistry</subject><ispartof>Catalysis letters, 2020-04, Vol.150 (4), p.930-938</ispartof><rights>The Author(s) 2019</rights><rights>COPYRIGHT 2020 Springer</rights><rights>Catalysis Letters is a copyright of Springer, (2019). All Rights Reserved. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c473t-1bcb968a29901f100c266818fcda2433a99d770168e07b6a1776b6b55bd0e18f3</citedby><cites>FETCH-LOGICAL-c473t-1bcb968a29901f100c266818fcda2433a99d770168e07b6a1776b6b55bd0e18f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Nemcsok, Tamás</creatorcontrib><creatorcontrib>Rapi, Zsolt</creatorcontrib><creatorcontrib>Bagi, Péter</creatorcontrib><creatorcontrib>Oláh, Attila</creatorcontrib><creatorcontrib>Keglevich, György</creatorcontrib><creatorcontrib>Bakó, Péter</creatorcontrib><title>The Synthesis of Hydrobenzoin-Based Monoaza Crown Ethers and Their Application as Recyclable Enantioselective Catalysts</title><title>Catalysis letters</title><addtitle>Catal Lett</addtitle><description>New recyclable monoaza-15-crown ethers have been synthesized starting from (
R
,
R
)-(+)- and (
S
,
S
)-(−)-hydrobenzoin. These macrocycles proved to be efficient and reusable phase transfer catalysts in a few asymmetric reactions under mild conditions. The asymmetric epoxidation of
trans
-chalcone took place with up to 81% ee, while using other chalcone derivatives, the products were formed with 68–88% ee. The hydrobenzoin-based lariat ethers were also tested in the cyclopropanation of a few electron deficient olefins using diethyl bromomalonate to afford the product with good enantioselectivities (54–75% ee). The catalysts were recovered by salt formation, followed by extraction, and were reused without the loss of the activity and effect on the enantioselectivity.
Graphic Abstract
The synthesis of hydrobenzoin-based monaza crown ethers and their application as recyclable enantioselective catalysts.</description><subject>Alkenes</subject><subject>Asymmetry</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Crown ethers</subject><subject>Cyclopropane compounds</subject><subject>Enantiomers</subject><subject>Epoxidation</subject><subject>Ethers</subject><subject>Industrial Chemistry/Chemical Engineering</subject><subject>Olefins</subject><subject>Organometallic Chemistry</subject><subject>Phase transfer catalysts</subject><subject>Physical Chemistry</subject><issn>1011-372X</issn><issn>1572-879X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kU1r3DAQhk1poWmaP9CToKcenI6sXck6bpdtE0gJ5ANyE2N5vFFwpK2kTer8-ip1oeQSdJAYnkfSzFtVnzgccwD1NXFYyqYGrmsQwEUNb6oDvlRN3Sp987acgfNaqObmffUhpTsA0Irrg-rx6pbY5eTzLSWXWBjYydTH0JF_Cs7X3zBRz34GH_AJ2TqGR882hY2Joe9ZkV1kq91udBazC55hYhdkJztiNxLbePSlnGgkm90DsTVmHKeU08fq3YBjoqN_-2F1_X1ztT6pz85_nK5XZ7VdKJFr3tlOyxYbrYEPpVXbSNnydrA9NgshUOteKeCyJVCdRK6U7GS3XHY9UMHEYfV5vncXw689pWzuwj768qRphFRSiFYvCnU8U1scyTg_hBzRltXTvbPB0-BKfSXLRLkQEorw5YVQmEy_8xb3KZnTy4uXbDOzNoaUIg1mF909xslwMM_pmTk9U9Izf9Mzz5KYpVRgv6X4_9-vWH8AVDmclg</recordid><startdate>20200401</startdate><enddate>20200401</enddate><creator>Nemcsok, Tamás</creator><creator>Rapi, Zsolt</creator><creator>Bagi, Péter</creator><creator>Oláh, Attila</creator><creator>Keglevich, György</creator><creator>Bakó, Péter</creator><general>Springer US</general><general>Springer</general><general>Springer Nature B.V</general><scope>C6C</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>ISR</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>AFKRA</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope></search><sort><creationdate>20200401</creationdate><title>The Synthesis of Hydrobenzoin-Based Monoaza Crown Ethers and Their Application as Recyclable Enantioselective Catalysts</title><author>Nemcsok, Tamás ; Rapi, Zsolt ; Bagi, Péter ; Oláh, Attila ; Keglevich, György ; Bakó, Péter</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c473t-1bcb968a29901f100c266818fcda2433a99d770168e07b6a1776b6b55bd0e18f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkenes</topic><topic>Asymmetry</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Crown ethers</topic><topic>Cyclopropane compounds</topic><topic>Enantiomers</topic><topic>Epoxidation</topic><topic>Ethers</topic><topic>Industrial Chemistry/Chemical Engineering</topic><topic>Olefins</topic><topic>Organometallic Chemistry</topic><topic>Phase transfer catalysts</topic><topic>Physical Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nemcsok, Tamás</creatorcontrib><creatorcontrib>Rapi, Zsolt</creatorcontrib><creatorcontrib>Bagi, Péter</creatorcontrib><creatorcontrib>Oláh, Attila</creatorcontrib><creatorcontrib>Keglevich, György</creatorcontrib><creatorcontrib>Bakó, Péter</creatorcontrib><collection>Springer Nature OA Free Journals</collection><collection>CrossRef</collection><collection>Science in Context</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central</collection><collection>SciTech Premium Collection</collection><collection>Materials Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><jtitle>Catalysis letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nemcsok, Tamás</au><au>Rapi, Zsolt</au><au>Bagi, Péter</au><au>Oláh, Attila</au><au>Keglevich, György</au><au>Bakó, Péter</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The Synthesis of Hydrobenzoin-Based Monoaza Crown Ethers and Their Application as Recyclable Enantioselective Catalysts</atitle><jtitle>Catalysis letters</jtitle><stitle>Catal Lett</stitle><date>2020-04-01</date><risdate>2020</risdate><volume>150</volume><issue>4</issue><spage>930</spage><epage>938</epage><pages>930-938</pages><issn>1011-372X</issn><eissn>1572-879X</eissn><abstract>New recyclable monoaza-15-crown ethers have been synthesized starting from (
R
,
R
)-(+)- and (
S
,
S
)-(−)-hydrobenzoin. These macrocycles proved to be efficient and reusable phase transfer catalysts in a few asymmetric reactions under mild conditions. The asymmetric epoxidation of
trans
-chalcone took place with up to 81% ee, while using other chalcone derivatives, the products were formed with 68–88% ee. The hydrobenzoin-based lariat ethers were also tested in the cyclopropanation of a few electron deficient olefins using diethyl bromomalonate to afford the product with good enantioselectivities (54–75% ee). The catalysts were recovered by salt formation, followed by extraction, and were reused without the loss of the activity and effect on the enantioselectivity.
Graphic Abstract
The synthesis of hydrobenzoin-based monaza crown ethers and their application as recyclable enantioselective catalysts.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s10562-019-03013-0</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 1011-372X |
| ispartof | Catalysis letters, 2020-04, Vol.150 (4), p.930-938 |
| issn | 1011-372X 1572-879X |
| language | eng |
| recordid | cdi_proquest_journals_2367633894 |
| source | Springer Link |
| subjects | Alkenes Asymmetry Catalysis Catalysts Chemistry Chemistry and Materials Science Crown ethers Cyclopropane compounds Enantiomers Epoxidation Ethers Industrial Chemistry/Chemical Engineering Olefins Organometallic Chemistry Phase transfer catalysts Physical Chemistry |
| title | The Synthesis of Hydrobenzoin-Based Monoaza Crown Ethers and Their Application as Recyclable Enantioselective Catalysts |
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