{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,13]],"date-time":"2026-01-13T06:27:57Z","timestamp":1768285677194,"version":"3.49.0"},"reference-count":55,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2024,1,10]],"date-time":"2024-01-10T00:00:00Z","timestamp":1704844800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry &amp; Biodiversity"],"published-print":{"date-parts":[[2024,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Regio\u2010 and stereoselective 1,3\u2010dipolar cycloadditions of <jats:italic>C<\/jats:italic>\u2010(3\u2010pyridyl)\u2010<jats:italic>N<\/jats:italic>\u2010phenylnitrone (<jats:bold>2<\/jats:bold>) with variedly substituted dipolarophiles (<jats:bold>3, 4<\/jats:bold>) were carried out to obtain substituted pyridyl\u2010isoxazolidines (<jats:bold>5<\/jats:bold>\u2013<jats:bold>8<\/jats:bold>). Reductive cleavage of pyridyl\u2010isoxazolidines (<jats:bold>5<\/jats:bold>\u2013<jats:bold>8<\/jats:bold>) with ammonium formate, methanol\u2212THF solvents, at ambient temperature, in the presence of Pd\/C provided a facile route for the synthesis of <jats:italic>\u03b2<\/jats:italic><jats:sup>3<\/jats:sup>\u2010and <jats:italic>\u03b2<\/jats:italic><jats:sup>2,3<\/jats:sup>\u2010amino alcohols (<jats:bold>9<\/jats:bold>\u2013<jats:bold>12<\/jats:bold>), with a substitution pattern having pronounced influence on torsional angles. The obtained compounds (<jats:bold>9<\/jats:bold>\u2013<jats:bold>12<\/jats:bold>) are valuable scaffolds which can be utilized for peptidomimetics. Thus, the present methodology for reductive opening of isoxazolidine ring avoids the disadvantages of using expensive apparatus and hazards involved in the use of hydrogen gas. The preferential formation of amino\u2010alcohols in case of bicyclic isoxazolidines (<jats:bold>8a<\/jats:bold>\u2013<jats:bold>c<\/jats:bold>), which precludes any recyclization is rationalized by DFT calculations.<\/jats:p>","DOI":"10.1002\/cbdv.202301323","type":"journal-article","created":{"date-parts":[[2023,12,20]],"date-time":"2023-12-20T12:33:15Z","timestamp":1703075595000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Facile Synthesis of Some New Peptidomimetic <i>\u03b2<\/i><sup>3<\/sup>\u2010and <i>\u03b2<\/i><sup>2,3<\/sup>\u2010Amino Alcohols Possessing Pyridyl Moiety via Reductive Ring Opening of Pyridyl\u2010isoxazolidines"],"prefix":"10.1002","volume":"21","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0815-0268","authenticated-orcid":false,"given":"Gagandeep","family":"Singh","sequence":"first","affiliation":[{"name":"Bio-Organic and Photochemistry Laboratory, Department of Pharmaceutical Sciences Guru Nanak Dev University  Amritsar 143 005 Punjab India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Naman","family":"Gupta","sequence":"additional","affiliation":[{"name":"Bio-Organic and Photochemistry Laboratory, Department of Pharmaceutical Sciences Guru Nanak Dev University  Amritsar 143 005 Punjab India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nidhi","family":"Sethi","sequence":"additional","affiliation":[{"name":"Bio-Organic and Photochemistry Laboratory, Department of Pharmaceutical Sciences Guru Nanak Dev University  Amritsar 143 005 Punjab India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Vivek","family":"Gupta","sequence":"additional","affiliation":[{"name":"Post-Graduate Department of Physics University of Jammu  Jammu Tawi 180 006 India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tilak","family":"Raj","sequence":"additional","affiliation":[{"name":"Toxicology Division Forensic Science Laboratory  Mohali 160 059 Punjab India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4992-4063","authenticated-orcid":false,"given":"Mohan Paul Singh","family":"Ishar","sequence":"additional","affiliation":[{"name":"Bio-Organic and Photochemistry Laboratory, Department of Pharmaceutical Sciences Guru Nanak Dev University  Amritsar 143 005 Punjab India"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2024,1,10]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00543"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00387"},{"key":"e_1_2_7_4_1","unstructured":"\u00a0"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0431713"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo1000065"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b02574"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c02301"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201600582"},{"key":"e_1_2_7_10_1","unstructured":"\u00a0"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2015.12.032"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2016.09.011"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2017.05.032"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2016.12.052"},{"key":"e_1_2_7_15_1","unstructured":"\u00a0"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00253-005-0155-y"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.2174\/0929867024606759"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/0471698482"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.2174\/092986730610220401155105"},{"key":"e_1_2_7_20_1","unstructured":"\u00a0"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.2174\/138161210793292555"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.201100093"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr000045i"},{"key":"e_1_2_7_24_1","unstructured":"\u00a0"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.2174\/0929867302666220218001506"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00058a007"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0143-4179(97)90073-1"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/3527601902"},{"key":"e_1_2_7_29_1","unstructured":"\u00a0"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2013.03.078"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF00370780"},{"key":"e_1_2_7_32_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0031-3955(16)33107-8"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/clc.4960131104"},{"key":"e_1_2_7_34_1","unstructured":"\u00a0"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570420603"},{"key":"e_1_2_7_36_2","first-page":"59","volume":"9","author":"Sethi N.","year":"2014","journal-title":"Res. Pharm. Sci."},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.1080\/22297928.2013.838430"},{"key":"e_1_2_7_38_1","unstructured":"\u00a0"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.3390\/molecules18066620"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2009.05.093"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2006.12.076"},{"key":"e_1_2_7_42_1","unstructured":"\u00a0"},{"key":"e_1_2_7_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19681010734"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19681010735"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19681010736"},{"key":"e_1_2_7_46_1","unstructured":"\u00a0"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1016\/0584-8539(72)80039-4"},{"key":"e_1_2_7_48_2","first-page":"279","volume-title":"Carbon-13 NMR Spectroscopy","author":"Breitmaier E.","year":"1987"},{"key":"e_1_2_7_49_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(00)00700-6"},{"key":"e_1_2_7_50_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3md00055a"},{"key":"e_1_2_7_51_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.196306331"},{"key":"e_1_2_7_52_1","unstructured":"The X-ray crystallographic data for compound10has been submitted to Cambridge crystallography Data Center (CCDC No.1476661)."},{"key":"e_1_2_7_53_1","unstructured":"\u00a0"},{"key":"e_1_2_7_54_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2013.09.064"},{"key":"e_1_2_7_55_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11434-013-5786-2"}],"container-title":["Chemistry &amp; Biodiversity"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbdv.202301323","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,3,11]],"date-time":"2025-03-11T23:24:46Z","timestamp":1741735486000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/cbdv.202301323"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,1,10]]},"references-count":55,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2024,2]]}},"alternative-id":["10.1002\/cbdv.202301323"],"URL":"https:\/\/doi.org\/10.1002\/cbdv.202301323","archive":["Portico"],"relation":{},"ISSN":["1612-1872","1612-1880"],"issn-type":[{"value":"1612-1872","type":"print"},{"value":"1612-1880","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,1,10]]},"assertion":[{"value":"2023-08-31","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-12-18","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-01-10","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202301323"}}