{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,10]],"date-time":"2026-04-10T20:20:49Z","timestamp":1775852449782,"version":"3.50.1"},"reference-count":98,"publisher":"Wiley","issue":"17","license":[{"start":{"date-parts":[[2007,4,20]],"date-time":"2007-04-20T00:00:00Z","timestamp":1177027200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2007,6,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A study of the reactivity pattern associated with zwitterionic allenolates \u201con water\u201d is reported. This study establishes the chemical basis for two organocatalyzed allenolate\u2010driven reaction networks operating \u201con water\u201d. The first one is a chemodifferentiating three building block (ABB\u2032) three\u2010component reaction (ABB\u2032 3CR) manifold comprising terminal alkynoates and aldehydes. The manifold produces propargylic enol ethers <jats:bold>3<\/jats:bold> with higher average efficiency than their homologues in organic solvents. The second one is a novel organocatalytic system elicited by the reaction of alkynoates and nitrones in the presence of tertiary amines or phosphines. While terminal alkynoates afford 2,3,5\u2010trisubstituted 2,3\u2010dihydroisoxazoles <jats:bold>5<\/jats:bold> and propargylic N\u2010hydroxylamines <jats:bold>6<\/jats:bold>, internal alkynoates selectively afford the 2,3,4,5\u2010tetrasusbstituted 2,3\u2010dihydroisoxazaole <jats:bold>10<\/jats:bold>. Importantly, in both cases, the 2,3\u2010dihydroisoxazole ring is obtained as a sole regioisomer.<\/jats:p>","DOI":"10.1002\/chem.200700227","type":"journal-article","created":{"date-parts":[[2007,4,20]],"date-time":"2007-04-20T11:40:15Z","timestamp":1177069215000},"page":"4823-4832","source":"Crossref","is-referenced-by-count":65,"title":["Dual Reactivity Pattern of Allenolates \u201cOn Water\u201d: The Chemical Basis for Efficient Allenolate\u2010Driven Organocatalytic Systems"],"prefix":"10.1002","volume":"13","author":[{"given":"David","family":"Gonz\u00e1lez\u2010Cruz","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"David","family":"Tejedor","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Pedro","family":"de\u2005Armas","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fernando","family":"Garc\u00eda\u2010Tellado","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2007,5,22]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar010065m"},{"key":"e_1_2_6_2_2","unstructured":"\u00a0"},{"key":"e_1_2_6_3_2","volume-title":"Handbook of Green Chemistry and Technology","year":"2002"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/op050227k"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020201)114:3<402::AID-ANGE402>3.0.CO;2-D"},{"key":"e_1_2_6_5_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020201)41:3<414::AID-ANIE414>3.0.CO;2-N"},{"key":"e_1_2_6_6_2","unstructured":"\u00a0"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00546a048"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar00006a001"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)81800-6"},{"key":"e_1_2_6_10_2","unstructured":"\u00a0"},{"key":"e_1_2_6_11_2","volume-title":"Organic Synthesis in Water","year":"1998"},{"key":"e_1_2_6_12_2","volume-title":"Water as a solvent for chemical reactions in Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes","author":"Breslow R.","year":"1998"},{"key":"e_1_2_6_13_2","unstructured":"\u00a0"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/B507207G"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr030009u"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr010122p"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200500959"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1039\/b305672d"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200462883"},{"key":"e_1_2_6_19_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462883"},{"key":"e_1_2_6_20_2","unstructured":"\u00a0"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/3527604677"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200400650"},{"key":"e_1_2_6_22_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200400650"},{"key":"e_1_2_6_23_2","volume-title":"Acc. 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The results of this study will be published at due time elsewhere."},{"key":"e_1_2_6_91_2","unstructured":"The experimentally observed bad catalytic activity of the Ph3P could be due to a phosphorous\u2010driven rearrangement of alkynoate9\u2009cto ethyl 2 3\u2010butadienoate [17]a poor dipolarophile and an excellent precursor of phosphorous\u2010containing allylic anionsIV(see Scheme\u20052)."},{"key":"e_1_2_6_92_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol051044l"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.200700227","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.200700227","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T19:59:12Z","timestamp":1760299152000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.200700227"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2007,5,22]]},"references-count":98,"journal-issue":{"issue":"17","published-print":{"date-parts":[[2007,6,4]]}},"alternative-id":["10.1002\/chem.200700227"],"URL":"https:\/\/doi.org\/10.1002\/chem.200700227","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2007,5,22]]}}}