{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,23]],"date-time":"2026-02-23T14:27:28Z","timestamp":1771856848916,"version":"3.50.1"},"reference-count":25,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2015,7,27]],"date-time":"2015-07-27T00:00:00Z","timestamp":1437955200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>An asymmetric annulation reaction of \u03b3-butenolides and cyclic 1-azadienes containing a 1,2-benzoisothiazole-1,1-dioxide motif has been studied, proceeding in a tandem Michael addition-aza-Michael addition sequence. Endo-type cycloadducts bearing fused tetracyclic skeletons were isolated in fair yields and with high enantioselectivity (up to &gt;99% ee) under the catalysis of modified cinchona alkaloid (DHQD)2PHAL. Besides,  exo-type diastereomers could be produced using \u03b2-isocupreidine (\u03b2-ICD) as the catalyst, though with moderate enantioselectivity.<\/jats:p>","DOI":"10.3390\/molecules200813642","type":"journal-article","created":{"date-parts":[[2015,7,28]],"date-time":"2015-07-28T02:12:37Z","timestamp":1438049557000},"page":"13642-13658","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":31,"title":["Diastereodivergent and Enantioselective [4+2] Annulations of  \u03b3-Butenolides with Cyclic 1-Azadienes"],"prefix":"10.3390","volume":"20","author":[{"given":"Chao","family":"Li","sequence":"first","affiliation":[{"name":"College of Pharmacy, Third Military Medical University, Chongqing 400038, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kun","family":"Jiang","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Third Military Medical University, Chongqing 400038, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ying-Chun","family":"Chen","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Third Military Medical University, Chongqing 400038, China"},{"name":"Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education,  West China School of Pharmacy, Sichuan University, Chengdu 610041, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2015,7,27]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"625","DOI":"10.1021\/cr60303a004","article-title":"Recent Advances in the Chemistry of Unsaturated Lactones","volume":"76","author":"Rao","year":"1976","journal-title":"Chem. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"9426","DOI":"10.1002\/anie.200903108","article-title":"The Renaissance of \u03b1-Methylene-\u03b3-butyrolactones: New Synthetic Approaches","volume":"48","author":"Kitson","year":"2009","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"For a review, see: \n\t\t          \n\t\t            \n\t\t              Jusseau\n\t\t              X.\n\t\t             \n\t\t            \n\t\t              Chabaud\n\t\t              L.\n\t\t            \n\t\t            \n\t\t              Guillou\n\t\t              C.\n\t\t            \n\t\t          \n\t\t          Synthesis of \u03b3-Butenolides and \u03b1,\u03b2-Unsaturated \u03b3-Butyrolactams by Addition of Vinylogous Nucleophiles to Michael Acceptors\n\t\t          Tetrahedron\n\t\t          2014\n\t\t          70\n\t\t          2595\n\t\t          2615\n\t\t        .","DOI":"10.1016\/j.tet.2014.01.057"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"7310","DOI":"10.1002\/anie.201303119","article-title":"Direct Catalytic Asymmetric Vinylogous Mannich-Type Reaction of \u03b3-Butenolides with Ketimines","volume":"52","author":"Yin","year":"2013","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1858","DOI":"10.1002\/anie.200906647","article-title":"Asymmetric Direct Vinylogous Aldol Reaction of Furanone Derivatives Catalyzed by an Axially Chiral Guanidine Base","volume":"49","author":"Ube","year":"2010","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"5327","DOI":"10.1002\/anie.201402332","article-title":"Direct Catalytic Asymmetric Vinylogous Conjugate Addition of Unsaturated Butyrolactones to \u03b1,\u03b2-Unsaturated Thioamides","volume":"53","author":"Yin","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"4572","DOI":"10.1021\/ja809723u","article-title":"Direct Asymmetric Michael Addition to Nitroalkenes: Vinylogous Nucleophilicity under Dinuclear Zinc Catalysis","volume":"131","author":"Trost","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1540","DOI":"10.1021\/ol200235j","article-title":"Highly Enantioselective Direct Vinylogous Michael Addition of \u03b3-Butenolide to Enals","volume":"13","author":"Quintard","year":"2011","journal-title":"Org. Lett."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"7713","DOI":"10.1002\/chem.201301332","article-title":"Organocatalytic Enantioselective Direct Vinylogous Michael Addition of \u03b3-Substituted Butenolides to 3-Aroyl Acrylates and 1,2-Diaroylethylenes","volume":"19","author":"Das","year":"2013","journal-title":"Chem. Eur. J."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"10069","DOI":"10.1002\/anie.201205872","article-title":"Highly Enantio- and Diastereoselective Reactions of \u03b3-Substituted Butenolides Through Direct Vinylogous Conjugate Additions","volume":"51","author":"Zhang","year":"2012","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"2439","DOI":"10.1039\/c2cc17777c","article-title":"Asymmetric Assembly of 2-Oxindole and \u03b1-Angelica Lactone Units to Construct Vicinal Quaternary Chiral Centers","volume":"48","author":"Huang","year":"2012","journal-title":"Chem. Commun."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"15277","DOI":"10.1002\/chem.201203180","article-title":"Catalytic Asymmetric Direct Vinylogous Michael Addition of Deconjugated Butenolides to Maleimides for the Construction of Quaternary Stereogenic Centers","volume":"18","author":"Manna","year":"2012","journal-title":"Chem. Eur. J."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1627","DOI":"10.1039\/C3SC53102C","article-title":"Remarkable Influence of Secondary Catalyst Site on Enantioselective Desymmetrization of Cyclopentenedione","volume":"5","author":"Manna","year":"2014","journal-title":"Chem. Sci."},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"An example with the related \u03b1, \u03b2-unsaturated \u03b3-butyrolactam has been reported, see: \n\t\t\t          \n\t\t\t            \n\t\t\t              Jiang\n\t\t\t              X.\n\t\t\t            \n\t\t\t            \n\t\t\t              Liu\n\t\t\t              L.\n\t\t\t            \n\t\t\t            \n\t\t\t              Zhang\n\t\t\t              P.\n\t\t\t            \n\t\t\t            \n\t\t\t              Zhong\n\t\t\t              Y.\n\t\t\t            \n\t\t\t            \n\t\t\t              Wang\n\t\t\t              R.\n\t\t\t            \n\t\t\t          \n\t\t\t          Catalytic Asymmetric \u03b2,\u03b3 Activation of \u03b1,\u03b2-Unsaturated \u03b3-Butyrolactams: Direct Approach to \u03b2,\u03b3-Functionalized Dihydropyranopyrrolidin-2-ones\n\t\t\t          Angew. Chem. Int. Ed.\n\t\t\t          2013\n\t\t\t          52\n\t\t\t          11329\n\t\t\t          11333\n\t\t\t          10.1002\/anie.201302622\n\t\t\t          23929785\n\t\t\t        .","DOI":"10.1002\/anie.201302622"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"720","DOI":"10.1021\/ol100014m","article-title":"Direct Asymmetric Allylic Alkylation of Butenolides with Morita-Baylis-Hillman Carbonates","volume":"12","author":"Cui","year":"2010","journal-title":"Org. Lett."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"14173","DOI":"10.1002\/anie.201307460","article-title":"Trienamines Derived from Interrupted Cyclic 2,5-Dienones: Remote \u03b4,\u03b5-C=C Bond Activation for Asymmetric Inverse-Electron-Demand Aza-Diels-Alder Reaction","volume":"52","author":"Feng","year":"2013","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"3986","DOI":"10.1021\/ol501814p","article-title":"\u03b2,\u03b3-Regioselective Inverse-Electron-Demand Aza-Diels-Alder Reactions with \u03b1,\u03b2-Unsaturated Aldehydes via Dienamine Catalysis","volume":"16","author":"Gu","year":"2014","journal-title":"Org. Lett."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"6206","DOI":"10.1021\/ol4030474","article-title":"1-Azadienes as Regio- and Chemoselective Dienophiles in Aminocatalytic Asymmetric Diels-Alder Reaction","volume":"15","author":"Ma","year":"2013","journal-title":"Org. Lett."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"6245","DOI":"10.1002\/anie.201403753","article-title":"Asymmetric [5 + 3] Formal Cycloadditions with Cyclic Enones through Cascade Dienamine-dDienamine Catalysis","volume":"53","author":"Yin","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"For a review, see: \n\t\t\t\t          \n\t\t\t\t            \n\t\t\t\t              Siau\n\t\t\t\t              W.Y.\n\t\t\t\t            \n\t\t\t\t            \n\t\t\t\t              Wang\n\t\t\t\t              J.\n\t\t\t\t            \n\t\t\t\t          \n\t\t\t\t          Asymmetric organocatalytic reactions by bifunctional amine-thioureas\n\t\t\t\t          Catal. Sci. Technol.\n\t\t\t\t          2011\n\t\t\t\t          1\n\t\t\t\t          1298\n\t\t\t\t          1310\n\t\t\t\t          10.1039\/c1cy00271f\n\t\t\t\t        .","DOI":"10.1039\/c1cy00271f"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"10219","DOI":"10.1021\/ja992655+","article-title":"Chiral Amine-Catalyzed Asymmetric Baylis-Hillman Reaction: A Reliable Route to Highly Enantiomerically Enriched (\u03b1-Methylene-\u03b2-hydroxy)esters","volume":"121","author":"Iwabuchi","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"12653","DOI":"10.1002\/chem.201302665","article-title":"\u03b1-Isocupreine, an Enantiocomplementary Catalyst of \u03b2-Isocupreidine","volume":"19","author":"Nakamoto","year":"2013","journal-title":"Chem. Eur. J."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"621","DOI":"10.1021\/ar030048s","article-title":"Asymmetric Organic Catalysis with Modified Cinchona Alkaloids","volume":"37","author":"Tian","year":"2004","journal-title":"Acc. Chem. Res."},{"key":"ref_24","unstructured":"CCDC 1054121 (4a) and 1054131 (5a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via http:\/\/www.ccdc.cam.ac.uk\/conts\/retrieving.html."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"9971","DOI":"10.1002\/anie.200804183","article-title":"Organocatalytic Asymmetric Inverse-Electron-Demand Aza-Diels-Alder Reaction of N-Sulfonyl-1-aza-1,3-butadienes and Aldehydes","volume":"47","author":"Han","year":"2008","journal-title":"Angew. Chem. Int. Ed."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/20\/8\/13642\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T20:49:47Z","timestamp":1760215787000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/20\/8\/13642"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,7,27]]},"references-count":25,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2015,8]]}},"alternative-id":["molecules200813642"],"URL":"https:\/\/doi.org\/10.3390\/molecules200813642","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2015,7,27]]}}}