{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,10]],"date-time":"2026-09-10T19:11:19Z","timestamp":1789067479403,"version":"build-2803163510"},"reference-count":72,"publisher":"Wiley","issue":"41","license":[{"start":{"date-parts":[[2023,6,7]],"date-time":"2023-06-07T00:00:00Z","timestamp":1686096000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100010663","name":"H2020 European Research Council","doi-asserted-by":"publisher","award":["CoG 682002"],"award-info":[{"award-number":["CoG 682002"]}],"id":[{"id":"10.13039\/100010663","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002428","name":"Austrian Science Fund","doi-asserted-by":"publisher","award":["P32607"],"award-info":[{"award-number":["P32607"]}],"id":[{"id":"10.13039\/501100002428","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100006012","name":"Christian Doppler Forschungsgesellschaft","doi-asserted-by":"publisher","award":["EnODD"],"award-info":[{"award-number":["EnODD"]}],"id":[{"id":"10.13039\/501100006012","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2023,7,20]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    <jats:italic>p<\/jats:italic>\n                    \u2010Toluenesulfonyl (Tosyl) and nitrobenzenesulfonyl (Nosyl) are two of the most common sulfonyl protecting groups for amines in contemporary organic synthesis. While\n                    <jats:italic>p<\/jats:italic>\n                    \u2010toluenesulfonamides are known for their high stability\/robustness, their use in multistep synthesis is plagued by difficult removal. Nitrobenzenesulfonamides, on the other hand, are easily cleaved but display limited stability to various reaction conditions. In an effort to resolve this predicament, we herein present a new sulfonamide protecting group, which we term Nms. Initially developed through in silico studies, Nms\u2010amides overcome these previous limitations and leave no room for compromise. We have investigated the incorporation, robustness and cleavability of this group and found it to be superior to traditional sulfonamide protecting groups in a broad range of case studies.\n                  <\/jats:p>","DOI":"10.1002\/chem.202301312","type":"journal-article","created":{"date-parts":[[2023,6,8]],"date-time":"2023-06-08T00:13:37Z","timestamp":1686183217000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":30,"title":["Nms\u2010Amides: An Amine Protecting Group with Unique Stability and Selectivity"],"prefix":"10.1002","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2674-0165","authenticated-orcid":false,"given":"Philipp","family":"Spie\u00df","sequence":"first","affiliation":[{"name":"Institute of Organic Chemistry University of Vienna  W\u00e4hringer Stra\u00dfe 38 1090 Vienna Austria"},{"name":"Vienna Doctoral School in Chemistry University of Vienna  W\u00e4hringer Stra\u00dfe 42 1090 Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6127-4011","authenticated-orcid":false,"given":"Ana","family":"Sirvent","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry University of Vienna  W\u00e4hringer Stra\u00dfe 38 1090 Vienna Austria"},{"name":"Christian-Doppler Laboratory for Entropy-Oriented Drug Design University of Vienna  Josef-Holaubek-Platz\u20052 1090 Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8949-2958","authenticated-orcid":false,"given":"Irmgard","family":"Tiefenbrunner","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry University of Vienna  W\u00e4hringer Stra\u00dfe 38 1090 Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jules","family":"Sargueil","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry University of Vienna  W\u00e4hringer Stra\u00dfe 38 1090 Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8372-7982","authenticated-orcid":false,"given":"Anthony J.","family":"Fernandes","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry University of Vienna  W\u00e4hringer Stra\u00dfe 38 1090 Vienna Austria"},{"name":"Christian-Doppler Laboratory for Entropy-Oriented Drug Design University of Vienna  Josef-Holaubek-Platz\u20052 1090 Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0745-6134","authenticated-orcid":false,"given":"Ana","family":"Arroyo\u2010Bond\u00eda","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry University of Vienna  W\u00e4hringer Stra\u00dfe 38 1090 Vienna 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Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2578-6260","authenticated-orcid":false,"given":"Saad","family":"Shaaban","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry University of Vienna  W\u00e4hringer Stra\u00dfe 38 1090 Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8895-9969","authenticated-orcid":false,"given":"Daniel","family":"Kaiser","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry University of Vienna  W\u00e4hringer Stra\u00dfe 38 1090 Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3643-0718","authenticated-orcid":false,"given":"Nuno","family":"Maulide","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry University of Vienna  W\u00e4hringer Stra\u00dfe 38 1090 Vienna Austria"},{"name":"Christian-Doppler Laboratory for Entropy-Oriented Drug Design University of Vienna  Josef-Holaubek-Platz\u20052 1090 Vienna Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,6,7]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.0c00754"},{"key":"e_1_2_8_2_1","volume-title":"Amines","author":"Lawrence S. 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Hoboken NJ USA 2007 pp. 136\u2013233."},{"key":"e_1_2_8_37_1","unstructured":"DFT calculations on other sulfonamides such as secondary sulfonamides showed the Meisenheimer complex as a transition state."},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/0022-328X(87)80383-2"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2007.02.020"},{"key":"e_1_2_8_40_1","unstructured":"No signs of hydrolysis were observed in an NMR study in the presence of water for several days."},{"key":"e_1_2_8_41_1","unstructured":"For details see the Supporting Information."},{"key":"e_1_2_8_42_1","unstructured":"Lower temperatures avoided the formation of benzaldehydes."},{"key":"e_1_2_8_43_1","unstructured":"Deposition Numbers2244498 (for28) 2244499 (for2\u2009aa) 2244500 (for2\u2009ai) 2244501 (for2\u2009n) 2244502 (for41) 2244503 (for6) 2244504 (for2\u2009ag) 2244505 (for2\u2009v) 2244506 (for2\u2009o) 2244507 (for5) 2244508 (for2\u2009h) 2244698 (for2\u2009ak) contain(s) the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structures service."},{"key":"e_1_2_8_44_1","unstructured":"We found that treatment with K2CO3in MeOH can also lead to deprotection. This reactivity however is exclusive to primary alcohols as tertiary alkoxides were found not to react with Nms-amides (see Scheme\u20055B). 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