Brønsted Acid versus Phase‐Transfer Catalysis in the Enantioselective Transannular Aminohalogenation of Enesultams
We have studied the enantioselective transannular aminohalogenation reaction of unsaturated medium‐sized cyclic benzosulfonamides by using both chiral Brønsted acid and phase‐transfer catalysis. Under optimized conditions, a variety of bicyclic adducts can be obtained with good yields and high enant...
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| Veröffentlicht in: | Chemistry : a European journal 2022-11, Vol.28 (62), p.e202202267-n/a |
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| creator | Luis‐Barrera, Javier Rodriguez, Sandra Uria, Uxue Reyes, Efraim Prieto, Liher Carrillo, Luisa Pedrón, Manuel Tejero, Tomás Merino, Pedro Vicario, Jose L. |
| description | We have studied the enantioselective transannular aminohalogenation reaction of unsaturated medium‐sized cyclic benzosulfonamides by using both chiral Brønsted acid and phase‐transfer catalysis. Under optimized conditions, a variety of bicyclic adducts can be obtained with good yields and high enantioselectivities. The mechanism of the reaction was also studied by using computational tools; we observed that the reaction involves the participation of a conformer of the nine‐membered cyclic substrate with planar chirality in which the stereochemical outcome is controlled by the relative reactivity of the two pseudorotational enantiomers when interacting with the chiral catalyst.
Stereocontrol: We have studied the enantioselective transannular aminohalogenation of unsaturated medium‐sized cyclic benzosulfonamides by using both chiral Brønsted acid and phase‐transfer catalysis. The mechanism of the reaction was also studied by using computational tools; we observed that the key step for stereocontrol involves the participation of an interconverting planar chiral conformer of the nine‐membered cyclic starting material |
| doi_str_mv | 10.1002/chem.202202267 |
| format | Article |
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Stereocontrol: We have studied the enantioselective transannular aminohalogenation of unsaturated medium‐sized cyclic benzosulfonamides by using both chiral Brønsted acid and phase‐transfer catalysis. The mechanism of the reaction was also studied by using computational tools; we observed that the key step for stereocontrol involves the participation of an interconverting planar chiral conformer of the nine‐membered cyclic starting material</description><identifier>ISSN: 0947-6539</identifier><identifier>ISSN: 1521-3765</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202202267</identifier><identifier>PMID: 36111677</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Acids ; Adducts ; asymmetric catalysis ; Catalysis ; Catalysts ; Chemistry ; Chirality ; computational chemistry ; Computer applications ; electrophilic addition ; ELF ; Enantiomers ; medium-ring compounds ; Software ; Stereoisomerism ; Substrates ; transannular reactions</subject><ispartof>Chemistry : a European journal, 2022-11, Vol.28 (62), p.e202202267-n/a</ispartof><rights>2022 Wiley‐VCH GmbH</rights><rights>2022 Wiley-VCH GmbH.</rights><rights>2022. This article is published under http://creativecommons.org/licenses/by-nc-nd/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4697-2c6d00aa870917909f486c02b6f54621e60cd2fda003a5d19be743aafb3bc22d3</citedby><cites>FETCH-LOGICAL-c4697-2c6d00aa870917909f486c02b6f54621e60cd2fda003a5d19be743aafb3bc22d3</cites><orcidid>0000-0003-0372-7005 ; 0000-0003-4249-6748 ; 0000-0001-6557-1777 ; 0000-0001-7965-7168 ; 0000-0002-2202-3460 ; 0000-0003-2038-9925 ; 0000-0001-5208-6780 ; 0000-0003-3433-6701</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.202202267$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.202202267$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,780,784,885,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36111677$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Luis‐Barrera, Javier</creatorcontrib><creatorcontrib>Rodriguez, Sandra</creatorcontrib><creatorcontrib>Uria, Uxue</creatorcontrib><creatorcontrib>Reyes, Efraim</creatorcontrib><creatorcontrib>Prieto, Liher</creatorcontrib><creatorcontrib>Carrillo, Luisa</creatorcontrib><creatorcontrib>Pedrón, Manuel</creatorcontrib><creatorcontrib>Tejero, Tomás</creatorcontrib><creatorcontrib>Merino, Pedro</creatorcontrib><creatorcontrib>Vicario, Jose L.</creatorcontrib><title>Brønsted Acid versus Phase‐Transfer Catalysis in the Enantioselective Transannular Aminohalogenation of Enesultams</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>We have studied the enantioselective transannular aminohalogenation reaction of unsaturated medium‐sized cyclic benzosulfonamides by using both chiral Brønsted acid and phase‐transfer catalysis. Under optimized conditions, a variety of bicyclic adducts can be obtained with good yields and high enantioselectivities. The mechanism of the reaction was also studied by using computational tools; we observed that the reaction involves the participation of a conformer of the nine‐membered cyclic substrate with planar chirality in which the stereochemical outcome is controlled by the relative reactivity of the two pseudorotational enantiomers when interacting with the chiral catalyst.
Stereocontrol: We have studied the enantioselective transannular aminohalogenation of unsaturated medium‐sized cyclic benzosulfonamides by using both chiral Brønsted acid and phase‐transfer catalysis. 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Stereocontrol: We have studied the enantioselective transannular aminohalogenation of unsaturated medium‐sized cyclic benzosulfonamides by using both chiral Brønsted acid and phase‐transfer catalysis. The mechanism of the reaction was also studied by using computational tools; we observed that the key step for stereocontrol involves the participation of an interconverting planar chiral conformer of the nine‐membered cyclic starting material</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>36111677</pmid><doi>10.1002/chem.202202267</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0003-0372-7005</orcidid><orcidid>https://orcid.org/0000-0003-4249-6748</orcidid><orcidid>https://orcid.org/0000-0001-6557-1777</orcidid><orcidid>https://orcid.org/0000-0001-7965-7168</orcidid><orcidid>https://orcid.org/0000-0002-2202-3460</orcidid><orcidid>https://orcid.org/0000-0003-2038-9925</orcidid><orcidid>https://orcid.org/0000-0001-5208-6780</orcidid><orcidid>https://orcid.org/0000-0003-3433-6701</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Acids Adducts asymmetric catalysis Catalysis Catalysts Chemistry Chirality computational chemistry Computer applications electrophilic addition ELF Enantiomers medium-ring compounds Software Stereoisomerism Substrates transannular reactions |
| title | Brønsted Acid versus Phase‐Transfer Catalysis in the Enantioselective Transannular Aminohalogenation of Enesultams |
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