%0 Journal Article %1 ISI:000295872200031 %A Abaee, M. Saeed %A Mojtahedi, Mohammad M. %A Rezaei, M. Taghi %A Khavasi, Hamid Reza %C HAJDRIHOVA 19, LJUBLJANA 1000, SLOVENIA %D 2011 %I SLOVENSKO KEMIJSKO DRUSTVO %J ACTA CHIMICA SLOVENICA %K Diels-Alder Lewis acid catalysis; cycloaddition} dehydrodecalines; dienes; reaction; {Styrylcyclohexenone %N 3 %P 605-610 %T Diels-Alder Reactions of Styrylcyclohexenones: an Efficient Procedure for the Synthesis of Substituted Dehydrodecaline Derivatives %V 58 %X The Diels-Alder reaction of styrylcyclohex-2-enone derivatives 1 with N-phenylmaleimide was shown to be an efficient pathway for the synthesis of substituted dehydrodecaline derivatives. At elevated temperatures, mixtures of endo/exo adducts were formed, while in the presence of TiCl(4) exclusive formation of the endo stereoisomer was observed. Spectroscopic analysis and X-ray crystallography confirmed the formation of the endo adducts.

@article{ISI:000295872200031, abstract = {{The Diels-Alder reaction of styrylcyclohex-2-enone derivatives 1 with N-phenylmaleimide was shown to be an efficient pathway for the synthesis of substituted dehydrodecaline derivatives. At elevated temperatures, mixtures of endo/exo adducts were formed, while in the presence of TiCl(4) exclusive formation of the endo stereoisomer was observed. Spectroscopic analysis and X-ray crystallography confirmed the formation of the endo adducts.}}, added-at = {2017-05-10T15:29:29.000+0200}, address = {{HAJDRIHOVA 19, LJUBLJANA 1000, SLOVENIA}}, affiliation = {{Abaee, MS (Reprint Author), Chem \& Chem Engn Res Ctr Iran, POB 14335-186, Tehran, Iran. Abaee, M. Saeed; Mojtahedi, Mohammad M., Chem \& Chem Engn Res Ctr Iran, Tehran, Iran. Rezaei, M. Taghi, Islamic Azad Univ, Dept Chem, Saveh Branch, Saveh, Iran. Khavasi, Hamid Reza, Shahid Beheshti Univ, Dept Chem, GC, Tehran 1983963113, Iran.}}, author = {Abaee, M. Saeed and Mojtahedi, Mohammad M. and Rezaei, M. Taghi and Khavasi, Hamid Reza}, author-email = {{abaee@ccerci.ac.ir mojtahedi@ccerci.ac.ir}}, biburl = {https://www.bibsonomy.org/bibtex/238bebcd841f83b3af034045011bdc66e/hkhavasi}, cited-references = {{Abaee MS, 2008, SYNTHESIS-STUTTGART, P2122, DOI 10.1055/s-2008-1067114. Abaee MS, 2007, SYNTHESIS-STUTTGART, P3339, DOI 10.1055/s-2007-990806. Abaee MS, 2005, ORG LETT, V7, P5893, DOI 10.1021/o1052506y. Abaee MS, 2005, SYNLETT, P2317, DOI 10.1055/s-2005-872656. Asano M, 2005, SYNLETT, P1539, DOI 10.1055/s-2005-869843. Asano M, 2006, J ORG CHEM, V71, P6942, DOI 10.1021/jo0610208. Bella M, 2004, TETRAHEDRON, V60, P4821, DOI 10.1016/j.tet.2004.04.007. Bhargava G, 2005, EUR J ORG CHEM, P2397, DOI 10.1002/ejoc.200500013. Bhargava G, 2008, TETRAHEDRON, V64, P6801, DOI 10.1016/j.tet.2008.04.087. BOLS M, 1995, CHEM REV, V95, P1253, DOI 10.1021/cr00037a006. Born S, 2008, SYNLETT, P2877, DOI 10.1055/s-0028-1083501. Brummond KM, 2005, TETRAHEDRON, V61, P6180, DOI 10.1016/j.tet.2005.03.141. Constantino MG, 2008, TETRAHEDRON LETT, V49, P1393, DOI 10.1016/j.tetlet.2007.12.079. Davenport A. J., 2004, J CHEM SOC DA, P1481. Diels O, 1928, LIEBIGS ANN CHEM, V460, P98. Fensterbank L, 1997, SYNTHESIS-STUTTGART, P813. Fringuelli F., 2002, DIELS ALDER REACTION, P1. Hsu CC, 2009, TETRAHEDRON, V65, P2824, DOI 10.1016/j.tet.2008.12.082. Jana CK, 2008, CHEM-EUR J, V14, P6326, DOI 10.1002/chem.200800903. Jimenez-Alonso S, 2008, TETRAHEDRON, V64, P8938, DOI 10.1016/j.tet.2008.06.057. Kang JM, 1997, NATURE, V385, P50, DOI 10.1038/385050a0. Kang JM, 1998, J AM CHEM SOC, V120, P7389, DOI 10.1021/ja980927n. McGilvra JD, 2004, SYNLETT, P2440, DOI 10.1055/s-2004-834799. Mojtahedi MM, 2006, CAN J CHEM, V84, P429, DOI 10.1139/V06-024. Mojtahedi MM, 2008, MONATSH CHEM, V139, P917, DOI 10.1007/s00706-007-0847-3. Mojtahedi MM, 2007, ORG LETT, V9, P2791, DOI 10.1021/ol070894t. Mojtahedi MM, 2009, TETRAHEDRON LETT, V50, P2322, DOI 10.1016/j.tetlet.2009.02.199. Muller A, 2009, ACTA CHIM SLOV, V56, P535. Oppolzer W., 1991, COMPREHENSIVE ORGANI, V5, P315, DOI DOI 10.1016/B978-0-08-052349-1.00128-1. Palomo C, 2003, J AM CHEM SOC, V125, P13942, DOI 10.1021/ja0368002. Phoenix S, 2008, J AM CHEM SOC, V130, P13989, DOI 10.1021/ja805097s. Reymond S, 2008, CHEM REV, V108, P5359, DOI 10.1021/cr078346g. Rickerby J, 2007, CHEM-EUR J, V13, P3354, DOI 10.1002/chem.200600851. Safaei-Ghomi J, 2004, ACTA CHIM SLOV, V51, P545. Sarotti AM, 2009, TETRAHEDRON, V65, P3502, DOI 10.1016/j.tet.2009.02.020. Souweha MS, 2007, ORG LETT, V9, P5163, DOI 10.1021/ol702202b. Ward DE, 2000, ORG LETT, V2, P3937, DOI 10.1021/010067235. Wessig P, 2008, CHEM REV, V108, P2051, DOI 10.1021/cr0783986. Winbush SM, 2008, J ORG CHEM, V73, P1818, DOI 10.1021/jo7024515. Yoshizawa M, 2006, SCIENCE, V312, P251, DOI 10.1126/science.1124985. You LF, 2008, ADV SYNTH CATAL, V350, P2885, DOI 10.1002/adsc.200800552.}}, doc-delivery-number = {{833GX}}, interhash = {004f5f5814deb8ce3aa4f212f48dec64}, intrahash = {38bebcd841f83b3af034045011bdc66e}, issn = {{1318-0207}}, journal = {{ACTA CHIMICA SLOVENICA}}, journal-iso = {{Acta Chim. Slov.}}, keywords = {Diels-Alder Lewis acid catalysis; cycloaddition} dehydrodecalines; dienes; reaction; {Styrylcyclohexenone}, keywords-plus = {{SOLVENT-FREE SYNTHESIS; ASSEMBLED MOLECULAR CAPSULE; ANTIBIOTIC ANTITUMOR AGENTS; BROMIDE ETHYL ETHERATE; ENANTIOSELECTIVE SYNTHESIS; TRICYCLIC CORE; MICROWAVE IRRADIATION; ALPHA-AMINONITRILES; ONE-POT; CYCLOADDITION}}, language = {{English}}, number = {{3}}, number-of-cited-references = {{41}}, pages = {{605-610}}, publisher = {{SLOVENSKO KEMIJSKO DRUSTVO}}, research-areas = {{Chemistry}}, times-cited = {{6}}, timestamp = {2017-05-10T15:29:29.000+0200}, title = {{Diels-Alder Reactions of Styrylcyclohexenones: an Efficient Procedure for the Synthesis of Substituted Dehydrodecaline Derivatives}}, type = {{Article}}, unique-id = {{ISI:000295872200031}}, usage-count-last-180-days = {{0}}, usage-count-since-2013 = {{1}}, volume = {{58}}, web-of-science-categories = {{Chemistry, Multidisciplinary}}, year = {{2011}} }