{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,3]],"date-time":"2026-10-03T01:47:26Z","timestamp":1790992046762,"version":"4.1.0"},"reference-count":42,"publisher":"Wiley","issue":"43","license":[{"start":{"date-parts":[[2006,10,16]],"date-time":"2006-10-16T00:00:00Z","timestamp":1160956800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2006,11,6]]},"DOI":"10.1002\/anie.200603496","type":"journal-article","created":{"date-parts":[[2006,10,17]],"date-time":"2006-10-17T06:00:13Z","timestamp":1161064813000},"page":"7230-7233","source":"Crossref","is-referenced-by-count":138,"title":["A Highly Efficient and Practical Method for Catalytic Asymmetric Vinylogous Mannich (AVM) Reactions"],"prefix":"10.1002","volume":"45","author":[{"given":"Emma L.","family":"Carswell","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marc L.","family":"Snapper","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Amir H.","family":"Hoveyda","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2006,10,30]]},"reference":[{"key":"e_1_2_2_1_2","unstructured":"For reviews on utility of stereoselective vinylogous Mannich reactions see:"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr990247i"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar950230w"},{"key":"e_1_2_2_4_2","unstructured":"For example see:"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00075a107"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja010577w"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.05.003"},{"key":"e_1_2_2_8_2","unstructured":"For a review of Mannich reactions see:"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar030231l"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja048607t"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0482435"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200462202"},{"key":"e_1_2_2_12_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462202"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200462757"},{"key":"e_1_2_2_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462757"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja060716f"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja061731n"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)01939-5"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja046185h"},{"key":"e_1_2_2_18_2","unstructured":"For related Ag\u2010catalyzed Mannich\u2010type reactions (not AVM) see:"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9802450"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja030033p"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja049388e"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol050910r"},{"key":"e_1_2_2_23_2","unstructured":"For determination of relative and absolute stereochemical identity of AVM products from reactions of3 see theSupporting Information."},{"key":"e_1_2_2_24_2","unstructured":"See theSupporting Informationfor all data."},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar020094c"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.2003.974"},{"key":"e_1_2_2_27_2","unstructured":"For example when carried out on a 0.5\u2010g (2.4\u2010mmol) scale AVM of2\u2009aand3proceeds to only 43\u2009% conversion (93\u2009%ee) in the absence ofiPrOH (>98\u2009% conv. 82\u2009% yield 91\u2009%eewith 1.1 equiv of the alcohol additive). Ag\u2010catalyzed AVM to afford4\u2009aproceeds to 97\u2009% conversion (87\u2009% yield) in 92\u2009%eewith 1.1 equivalents H2O (conditions in Table 1)."},{"key":"e_1_2_2_28_2","unstructured":"Relative and absolute stereochemical identity of products derived from5was established through an X\u2010ray crystal structure of6\u2009j(entry 5 Table 2). See theSupporting Informationfor details."},{"key":"e_1_2_2_29_2","unstructured":"For relative and absolute stereochemical identity of products derived from7 see theSupporting Information."},{"key":"e_1_2_2_30_2","unstructured":"Preliminary data indicate that the chiral Ag complex likely serves as a Lewis acid catalyst (vs. Ag enolate). For example there is ca. 30\u2009% conversion in the presence of 20 mol\u2009% of Et3N (synthesis of4\u2009awith 1 mol\u2009%1\u2009a \u221278\u2009\u00b0C)."},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol006464j"},{"key":"e_1_2_2_32_2","unstructured":"The C\uf8feN bond of chiral ligands do not undergo addition likely because of steric hinderance provided by the amino acid substituent."},{"key":"e_1_2_2_33_2","unstructured":"Pre\u2010association of the amide moiety with the siloxyfuran is also feasible; such an interaction would enhance enolsilane nucleophilicity and facilitate delivery; see:"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja047339w"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature05102"},{"key":"e_1_2_2_36_2","unstructured":"\u00a0"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0118744"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200352081"},{"key":"e_1_2_2_38_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200352081"},{"key":"e_1_2_2_39_2","unstructured":"Preliminary results show that the present procedure is applicable to AVM of aldimines derived from aliphatic aldehydes."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.200603496","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.200603496","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T13:50:56Z","timestamp":1697464256000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.200603496"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2006,10,30]]},"references-count":42,"journal-issue":{"issue":"43","published-print":{"date-parts":[[2006,11,6]]}},"alternative-id":["10.1002\/anie.200603496"],"URL":"https:\/\/doi.org\/10.1002\/anie.200603496","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2006,10,30]]}}}