{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T17:59:41Z","timestamp":1760551181916,"version":"3.40.5"},"reference-count":48,"publisher":"American Chemical Society (ACS)","issue":"15","license":[{"start":{"date-parts":[[2020,7,27]],"date-time":"2020-07-27T00:00:00Z","timestamp":1595808000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2020,7,27]],"date-time":"2020-07-27T00:00:00Z","timestamp":1595808000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2020,7,27]],"date-time":"2020-07-27T00:00:00Z","timestamp":1595808000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"name":"R?gion Champagne-Ardenne"},{"name":"Institut de Chimie Mol?culaire, Universit? de Reims"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Org. Chem."],"published-print":{"date-parts":[[2020,8,7]]},"DOI":"10.1021\/acs.joc.0c00801","type":"journal-article","created":{"date-parts":[[2020,7,27]],"date-time":"2020-07-27T04:36:22Z","timestamp":1595824582000},"page":"9585-9598","source":"Crossref","is-referenced-by-count":5,"title":["<i>cis<\/i>-Dihydroxylated \u03b1-Trifluoromethylated <i>N<\/i>,<i>O<\/i>-Acetal from <scp>l<\/scp>-Tartaric Acid: Synthesis of Tetrasubstituted Stereocenter via Diastereoselective Pictet-Spengler Cyclization of <i>N<\/i>-Acyliminium Ions"],"prefix":"10.1021","volume":"85","author":[{"given":"Abdelkhalek","family":"Ben Jamaa","sequence":"first","affiliation":[{"name":"Universit\u00e9 de Reims Champagne-Ardenne, CNRS, Institut de Chimie Mol\u00e9culaire de Reims UMR 7312, 51097 Reims, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mohammed","family":"Latrache","sequence":"additional","affiliation":[{"name":"Universit\u00e9 de Reims Champagne-Ardenne, CNRS, Institut de Chimie Mol\u00e9culaire de Reims UMR 7312, 51097 Reims, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Emmanuel","family":"Riguet","sequence":"additional","affiliation":[{"name":"Universit\u00e9 de Reims Champagne-Ardenne, CNRS, Institut de Chimie Mol\u00e9culaire de Reims UMR 7312, 51097 Reims, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0992-722X","authenticated-orcid":true,"given":"Fabienne","family":"Grellepois","sequence":"additional","affiliation":[{"name":"Universit\u00e9 de Reims Champagne-Ardenne, CNRS, Institut de Chimie Mol\u00e9culaire de Reims UMR 7312, 51097 Reims, France"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"316","published-online":{"date-parts":[[2020,7,27]]},"reference":[{"key":"ref1\/cit1a","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(00)00159-9"},{"key":"ref1\/cit1b","doi-asserted-by":"publisher","DOI":"10.1021\/cr0306182"},{"key":"ref1\/cit1c","doi-asserted-by":"publisher","DOI":"10.1021\/cr020083x"},{"key":"ref1\/cit1d","doi-asserted-by":"publisher","DOI":"10.1055\/s-0028-1083325"},{"key":"ref1\/cit1e","doi-asserted-by":"publisher","DOI":"10.1055\/s-0028-1083346"},{"key":"ref1\/cit1f","doi-asserted-by":"publisher","DOI":"10.1055\/s-0035-1562095"},{"key":"ref1\/cit1g","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00806"},{"key":"ref2\/cit2a","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201203153"},{"key":"ref2\/cit2b","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201403469"},{"key":"ref3\/cit3a","doi-asserted-by":"publisher","DOI":"10.1021\/jo049672o"},{"key":"ref3\/cit3b","doi-asserted-by":"publisher","DOI":"10.1039\/b900189a"},{"key":"ref3\/cit3c","doi-asserted-by":"publisher","DOI":"10.1021\/jo101437b"},{"key":"ref4\/cit4a","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2005.10.028"},{"key":"ref4\/cit4b","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2007.06.111"},{"key":"ref5\/cit5a","doi-asserted-by":"publisher","DOI":"10.1039\/b105402n"},{"key":"ref5\/cit5b","doi-asserted-by":"publisher","DOI":"10.1021\/jo0205661"},{"key":"ref5\/cit5c","doi-asserted-by":"publisher","DOI":"10.1021\/jo051584w"},{"key":"ref6\/cit6","doi-asserted-by":"publisher","DOI":"10.1039\/B711844A"},{"key":"ref7\/cit7a","doi-asserted-by":"publisher","DOI":"10.3987\/COM-96-S12"},{"key":"ref7\/cit7b","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.200600124"},{"key":"ref7\/cit7c","doi-asserted-by":"publisher","DOI":"10.1021\/jo5002998"},{"key":"ref7\/cit7d","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.7b01814"},{"key":"ref8\/cit8","doi-asserted-by":"publisher","DOI":"10.1021\/jo8013403"},{"key":"ref9\/cit9a","doi-asserted-by":"publisher","DOI":"10.1021\/jo062016z"},{"key":"ref9\/cit9b","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201100551"},{"key":"ref10\/cit10","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc35037h"},{"key":"ref11\/cit11a","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)86391-2"},{"key":"ref11\/cit11b","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc46266h"},{"key":"ref12\/cit12","unstructured":"Heating the hydrated ketone 3 at the reflux of toluene with a heating mantle led to the\nformation of a new product [19F NMR (470 MHz, CD3OCD3) = \u221276.4 ppm; 19F NMR (470 MHz,\nCDCl3) = \u221276.1 ppm], which partially gives back\nto the hydrated ketone 3 [19F NMR (470 MHz,\nCD3OCD3) = \u221283.7 ppm; 19F\nNMR (470 MHz, CDCl3) = \u221283.9 ppm] after concentration\nof the reaction mixture. A small quadruplet at 188.3 ppm (J = 35.5 Hz) is detected in the 13C{1H} NMR spectrum (125.7 Mz, CDCl3) of the crude reaction\nmixture containing an average of 40% of 3 and 60% of\nthe new product."},{"key":"ref13\/cit13a","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2008.04.052"},{"key":"ref13\/cit13b","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2011.01.012"},{"key":"ref14\/cit14a","doi-asserted-by":"publisher","DOI":"10.1021\/ja00178a038"},{"key":"ref14\/cit14b","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200390291"},{"key":"ref15\/cit15a","doi-asserted-by":"publisher","DOI":"10.1039\/B407555B"},{"key":"ref15\/cit15b","doi-asserted-by":"publisher","DOI":"10.1055\/s-2006-926223"},{"key":"ref15\/cit15c","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2007.05.024"},{"key":"ref16\/cit16","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2011.07.021"},{"key":"ref17\/cit17","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2018.11.012"},{"key":"ref18\/cit18","doi-asserted-by":"publisher","DOI":"10.1021\/cr980379w"},{"key":"ref19\/cit19","doi-asserted-by":"publisher","DOI":"10.1021\/jo8004952"},{"key":"ref21\/cit21","unstructured":"Treatment of a 89:11\nmixture of diastereomers of deprotected O-acetyl-N,O-acetal 9 under acidic\nconditions led mostly to the triol 14 (isolated in 78%\nyield). Triol 14 was also obtained by acid hydrolysis\nof the protected N,O-acetal 5a and O-acetyl-N,O-acetal 6a in 99% and 66% yields, respectively.\nAll these results unambiguously confirmed the configurations of the\nstereocenters of the major stereoisomer of 9 as R,S,R (see the Experimental Section for details). It is noteworthy\nthat HCl is not effective to generate \u03b1-CF3 N-acylimium ions; see for example refs (7aandb)."},{"key":"ref22\/cit22","unstructured":"It is noteworthy that the reaction\nof N,O-acetal 5a with\nBF3\u00b7Et2O (10 equiv) in CH2Cl2 at rt for 24 h or CF3SO3H (10 equiv)\nin HFIP at 0 \u00b0C for 1 h led to the formation of compound 10 as the sole product; no traces of Pictet-Spengler derivatives\nwere detected in the 19F NMR spectra of the crude reaction\nmixture."},{"key":"ref23\/cit23","doi-asserted-by":"publisher","DOI":"10.1038\/s41570-017-0088"},{"key":"ref24\/cit24","unstructured":"The attempt\nto cyclize O-acetyl-N,O-acetal 6c using 10 equiv of BF3\u00b7Et2O in\nCH2Cl2 at rt led to a very complex mixture containing\nonly 19% of the desired Pictet-Spengler products 7c and epi-7c as a 38:62 mixture of diastereomers\naccording to the 19F NMR analysis of the crude reaction\nmixture."},{"key":"ref25\/cit25","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201105288"},{"key":"ref26\/cit26","doi-asserted-by":"publisher","DOI":"10.1039\/C9OB01363F"},{"key":"ref27\/cit27","doi-asserted-by":"publisher","DOI":"10.1039\/c0ob00136h"},{"key":"ref28\/cit28","doi-asserted-by":"publisher","DOI":"10.1021\/jm960083n"}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.0c00801","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,17]],"date-time":"2023-04-17T14:19:10Z","timestamp":1681741150000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/acs.joc.0c00801"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,7,27]]},"references-count":48,"journal-issue":{"issue":"15","published-print":{"date-parts":[[2020,8,7]]}},"alternative-id":["10.1021\/acs.joc.0c00801"],"URL":"https:\/\/doi.org\/10.1021\/acs.joc.0c00801","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"type":"print","value":"0022-3263"},{"type":"electronic","value":"1520-6904"}],"subject":[],"published":{"date-parts":[[2020,7,27]]}}}