{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T14:57:55Z","timestamp":1760367475362,"version":"3.40.5"},"reference-count":52,"publisher":"American Chemical Society (ACS)","issue":"21","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Org. Lett."],"published-print":{"date-parts":[[2009,11,5]]},"DOI":"10.1021\/ol901760a","type":"journal-article","created":{"date-parts":[[2009,9,30]],"date-time":"2009-09-30T14:42:26Z","timestamp":1254321746000},"page":"4802-4805","source":"Crossref","is-referenced-by-count":17,"title":["Mechanistic Investigation on the Formation of Indolizines from 2-Enynylpyridines"],"prefix":"10.1021","volume":"11","author":[{"given":"Inma R.","family":"Lahoz","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Facultade de Qu\u00edmica, Campus Lagoas-Marcosende, 36310 Vigo, Spain"}]},{"given":"Cristina","family":"Sicre","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Facultade de Qu\u00edmica, Campus Lagoas-Marcosende, 36310 Vigo, Spain"}]},{"given":"Armando","family":"Navarro-V\u00e1zquez","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Facultade de Qu\u00edmica, Campus Lagoas-Marcosende, 36310 Vigo, Spain"}]},{"given":"Carlos Silva","family":"L\u00f3pez","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Facultade de Qu\u00edmica, Campus Lagoas-Marcosende, 36310 Vigo, Spain"}]},{"given":"Mar\u00eda-Magdalena","family":"Cid","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Facultade de Qu\u00edmica, Campus Lagoas-Marcosende, 36310 Vigo, Spain"}]}],"member":"316","published-online":{"date-parts":[[2009,9,30]]},"reference":[{"key":"ref1\/cit1a","doi-asserted-by":"crossref","first-page":"619","DOI":"10.1093\/oxfordjournals.jbchem.a021982","volume":"123","author":"Kitadokoro K.","year":"1998","journal-title":"J. Biochem."},{"key":"ref1\/cit1b","doi-asserted-by":"crossref","first-page":"4708","DOI":"10.1021\/jm800422v","volume":"51","author":"Oslund R. C.","year":"2008","journal-title":"J. Med. Chem."},{"key":"ref1\/cit1c","doi-asserted-by":"crossref","first-page":"1425","DOI":"10.1021\/jm00062a015","volume":"36","author":"Gubin J.","year":"1993","journal-title":"J. Med. Chem."},{"key":"ref2\/cit2a","doi-asserted-by":"crossref","first-page":"867","DOI":"10.1016\/j.ejmech.2003.08.001","volume":"38","author":"Gupta S. P.","year":"2003","journal-title":"Eur. J. Med. Chem."},{"key":"ref2\/cit2b","doi-asserted-by":"crossref","first-page":"3636","DOI":"10.1021\/jm960395q","volume":"39","author":"Hagishita S.","year":"1996","journal-title":"J. Med. Chem."},{"key":"ref3\/cit3","doi-asserted-by":"crossref","first-page":"3763","DOI":"10.1002\/1099-0690(200011)2000:22<3763::AID-EJOC3763>3.0.CO;2-S","author":"\u00d8stby O. B.","year":"2000","journal-title":"Eur. J. Org. Chem."},{"key":"ref4\/cit4a","doi-asserted-by":"crossref","first-page":"12206","DOI":"10.1021\/ja8020268","volume":"130","author":"Kim E.","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref4\/cit4b","doi-asserted-by":"crossref","first-page":"312","DOI":"10.1016\/j.jphotochem.2006.06.026","volume":"185","author":"Surpateanu G. G.","year":"2007","journal-title":"J. Photochem. Photobiol. A"},{"key":"ref4\/cit4c","doi-asserted-by":"crossref","first-page":"3939","DOI":"10.1016\/j.tet.2005.02.063","volume":"61","author":"Delattre F.","year":"2005","journal-title":"Tetrahedron"},{"key":"ref4\/cit4d","doi-asserted-by":"crossref","first-page":"1798","DOI":"10.1002\/hlca.200590141","volume":"88","author":"Retaru A. V.","year":"2005","journal-title":"Helv. Chim. Acta"},{"key":"ref5\/cit5","unstructured":"For a review, see:Behnisch, A.; Behnisch, P.; Eggenweiler, M.; Wallenhorst, T.Indolizine. Houben-Weyl;Thieme:Stuttgart, 1994; Vol.E6a\/2a, pp323\u2212450.See also recent examples:"},{"key":"ref5\/cit5a","doi-asserted-by":"crossref","first-page":"411","DOI":"10.1055\/s-0028-1087533","author":"Basavaiah D.","year":"2009","journal-title":"Synlett"},{"key":"ref5\/cit5b","doi-asserted-by":"crossref","first-page":"297","DOI":"10.3987\/COM-07-11197","volume":"75","author":"Niyomura O.","year":"2008","journal-title":"Heterocycles"},{"key":"ref5\/cit5c","doi-asserted-by":"crossref","first-page":"7742","DOI":"10.1021\/ja072718l","volume":"129","author":"Seregin I. V.","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5d","doi-asserted-by":"crossref","first-page":"9868","DOI":"10.1021\/ja072446m","volume":"129","author":"Schwier T.","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5e","doi-asserted-by":"crossref","first-page":"3433","DOI":"10.1021\/ol701464j","volume":"9","author":"Seregin I. V.","year":"2007","journal-title":"Org. Lett."},{"key":"ref5\/cit5f","doi-asserted-by":"crossref","first-page":"4547","DOI":"10.1021\/ol701973s","volume":"9","author":"Hardin A. R.","year":"2007","journal-title":"Org. Lett."},{"key":"ref5\/cit5g","doi-asserted-by":"crossref","first-page":"4463","DOI":"10.1021\/ol702084f","volume":"9","author":"Chuprakov S.","year":"2007","journal-title":"Org. Lett."},{"key":"ref5\/cit5h","doi-asserted-by":"crossref","first-page":"4323","DOI":"10.1021\/ol701886e","volume":"9","author":"Yan B.","year":"2007","journal-title":"Org. Lett."},{"key":"ref5\/cit5i","doi-asserted-by":"crossref","first-page":"1169","DOI":"10.1021\/ol0701971","volume":"9","author":"Smith C. R.","year":"2007","journal-title":"Org. Lett."},{"key":"ref5\/cit5j","doi-asserted-by":"crossref","first-page":"409","DOI":"10.1021\/ol062766v","volume":"9","author":"Liu Y.","year":"2007","journal-title":"Org. Lett."},{"key":"ref5\/cit5k","doi-asserted-by":"crossref","first-page":"7783","DOI":"10.1021\/jo070983j","volume":"72","author":"Yan B.","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref5\/cit5l","doi-asserted-by":"crossref","first-page":"6863","DOI":"10.1016\/j.tetlet.2007.07.180","volume":"48","author":"Kim I.","year":"2007","journal-title":"Tetrahedron Lett."},{"key":"ref5\/cit5m","doi-asserted-by":"crossref","first-page":"6034","DOI":"10.1016\/j.tetlet.2007.06.076","volume":"48","author":"Guazzelli G.","year":"2007","journal-title":"Tetrahedron Lett."},{"key":"ref5\/cit5n","doi-asserted-by":"crossref","first-page":"5739","DOI":"10.1016\/j.tetlet.2007.06.095","volume":"48","author":"Przewloka T.","year":"2007","journal-title":"Tetrahedron Lett."},{"key":"ref5\/cit5o","doi-asserted-by":"crossref","first-page":"3718","DOI":"10.1002\/ejoc.200700250","author":"Shen Y.-M.","year":"2007","journal-title":"Eur. J. Org. Chem."},{"key":"ref5\/cit5p","doi-asserted-by":"crossref","first-page":"2263","DOI":"10.1016\/j.tet.2006.12.063","volume":"63","author":"Lotter A. N. C.","year":"2007","journal-title":"Tetrahedron"},{"key":"ref5\/cit5q","doi-asserted-by":"crossref","first-page":"9114","DOI":"10.1021\/jo0615044","volume":"71","author":"Marchalin S.","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref6\/cit6","doi-asserted-by":"crossref","first-page":"2671","DOI":"10.1021\/ol0508173","volume":"7","author":"Hayford A.","year":"2005","journal-title":"Org. Lett."},{"key":"ref7\/cit7","doi-asserted-by":"crossref","first-page":"4305","DOI":"10.1021\/ol051860t","volume":"7","author":"Kaloko J.","year":"2005","journal-title":"Org. Lett."},{"key":"ref8\/cit8","doi-asserted-by":"crossref","first-page":"5737","DOI":"10.1021\/ol052512u","volume":"7","author":"Sicre C.","year":"2005","journal-title":"Org. Lett."},{"key":"ref9\/cit9a","doi-asserted-by":"crossref","first-page":"255","DOI":"10.1002\/anie.199402551","volume":"33","author":"Herges R.","year":"1994","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref9\/cit9b","doi-asserted-by":"crossref","first-page":"1572","DOI":"10.1021\/ja017227u","volume":"124","author":"Kimball D. B.","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref9\/cit9c","doi-asserted-by":"crossref","first-page":"13463","DOI":"10.1021\/ja027809r","volume":"124","author":"Kimball D. B.","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref10\/cit10","doi-asserted-by":"crossref","first-page":"3214","DOI":"10.1021\/jp0034426","volume":"105","author":"Herges R.","year":"2001","journal-title":"J. Phys. Chem. A"},{"key":"ref11\/cit11","doi-asserted-by":"crossref","first-page":"3758","DOI":"10.1021\/cr0300901","volume":"105","author":"Geuenich D.","year":"2005","journal-title":"Chem. Rev."},{"key":"ref12\/cit12","unstructured":"R = Me for computed structures (see the computational methods)."},{"key":"ref13\/cit13a","doi-asserted-by":"crossref","first-page":"B864","DOI":"10.1103\/PhysRev.136.B864","volume":"136","author":"Hohenberg P.","year":"1964","journal-title":"Phys. Rev."},{"key":"ref13\/cit13b","doi-asserted-by":"crossref","first-page":"A1133","DOI":"10.1103\/PhysRev.140.A1133","volume":"140","author":"Kohn W.","year":"1965","journal-title":"Phys. Rev. A"},{"key":"ref14\/cit14a","doi-asserted-by":"crossref","first-page":"3098","DOI":"10.1103\/PhysRevA.38.3098","volume":"38","author":"Becke A. D.","year":"1988","journal-title":"Phys. Rev. A"},{"key":"ref14\/cit14b","doi-asserted-by":"crossref","first-page":"5648","DOI":"10.1063\/1.464913","volume":"98","author":"Becke A. D.","year":"1993","journal-title":"J. Chem. Phys."},{"key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","volume":"37","author":"Lee C.","year":"1988","journal-title":"Phys. Rev. B."},{"key":"ref16\/cit16a","doi-asserted-by":"crossref","first-page":"2027","DOI":"10.1021\/cr00031a013","volume":"94","author":"Tomasi J.","year":"1994","journal-title":"Chem. Rev."},{"key":"ref16\/cit16b","doi-asserted-by":"crossref","first-page":"290","DOI":"10.1002\/(SICI)1096-987X(199802)19:3<290::AID-JCC3>3.0.CO;2-O","volume":"19","author":"Mineva T.","year":"1998","journal-title":"J. Comput. Chem."},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1021\/ar020270h","volume":"38","author":"Schreiner P. R.","year":"2005","journal-title":"Acc. Chem. Res."},{"key":"ref18\/cit18","doi-asserted-by":"crossref","first-page":"9047","DOI":"10.1063\/1.471637","volume":"104","author":"Bauernschmitt R.","year":"1996","journal-title":"J. Chem. Phys."},{"key":"ref19\/cit19","unstructured":"Gaussian 03, Rev. E.01:Frisch, M. J."},{"key":"ref19\/cit19a","unstructured":"Gaussian, Inc., Wallingford CT, 2004. See theSupporting Informationfor the full citation."},{"key":"ref20\/cit20","unstructured":"These values are, however, lower than the activation energies for ethylene isomerization since the diradical TS is stabilized by conjugation."},{"key":"ref21\/cit21","unstructured":"An alternative six-centered addition of MeOLi to the substrate could alleviate the ring strain at the transition state. The bond rotation in this alternative is, however, \u201clocked\u201d by Li coordination, rendering this mechanism noncompetitive."},{"key":"ref22\/cit22","unstructured":"Due to the nucleophilicity of the carbene intermediate, an electrophilic agent is required for successful trapping."},{"key":"ref23\/cit23","unstructured":"The particular reactivity of this carbene and further work on its cyclization to afford more complex indolizines are underway."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ol901760a","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,7]],"date-time":"2023-03-07T10:00:47Z","timestamp":1678183247000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ol901760a"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,9,30]]},"references-count":52,"journal-issue":{"issue":"21","published-print":{"date-parts":[[2009,11,5]]}},"alternative-id":["10.1021\/ol901760a"],"URL":"https:\/\/doi.org\/10.1021\/ol901760a","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"type":"print","value":"1523-7060"},{"type":"electronic","value":"1523-7052"}],"subject":[],"published":{"date-parts":[[2009,9,30]]}}}