%0 Journal Article %1 ISI:000366029500024 %A Abaee, M. Saeed %A Mobayen, Fatemeh %A Mojtahedi, Mohammad M. %A Saberi, Farveh %A Khavasi, Hamid Reza %C C/O ALAN R KATRITZKY, UNIV FLORIDA, DEPT CHEMISTRY, PO BOX 117200, GAINESVILLE, FL 32611 USA %D 2015 %I ARKAT USA INC %J ARKIVOC %K Diels-Alder aldol condensation; organocatalysis; reaction; stereoselectivity} {Tandem %N 7 %P 305-315 %R 10.3998/ark.5550190.p009.344 %T Et2NH/H2O catalyzed tandem aldol condensation - Diels-Alder cycloaddition sequence for the one-pot synthesis of (2R,3S)-rel-3-aryl-1,2,3,4,5,6,7,8-octahydro-6,6-dimethyl-8-oxo-2-naphth alenecarboxylates %X A tandem aldol condensation - Diels-Alder cycloaddition process is developed to combine isophorone (3,5,5-trimethyl-2-cyclohexen-1-one), aromatic aldehydes, and methyl acrylate in an efficient stereoselective one-pot synthesis of methyl (2R,3S)-rel-3-aryl-1,2,3,4,5,6,7,8-octahydro6,6- dimethyl-8-oxo-2-naphthalenecarboxylates using trace quantities of ammonium ions under aqueous conditions. Alternatively, the respective conjugated dienes which are formed in situ from the condensation of isophorone with the aldehydes can also react with methyl acrylate in a stepwise fashion leading to the same products.

@article{ISI:000366029500024, abstract = {{A tandem aldol condensation - Diels-Alder cycloaddition process is developed to combine isophorone (3,5,5-trimethyl-2-cyclohexen-1-one), aromatic aldehydes, and methyl acrylate in an efficient stereoselective one-pot synthesis of methyl (2R,3S)-rel-3-aryl-1,2,3,4,5,6,7,8-octahydro6,6- dimethyl-8-oxo-2-naphthalenecarboxylates using trace quantities of ammonium ions under aqueous conditions. Alternatively, the respective conjugated dienes which are formed in situ from the condensation of isophorone with the aldehydes can also react with methyl acrylate in a stepwise fashion leading to the same products.}}, added-at = {2017-05-10T15:29:29.000+0200}, address = {{C/O ALAN R KATRITZKY, UNIV FLORIDA, DEPT CHEMISTRY, PO BOX 117200, GAINESVILLE, FL 32611 USA}}, affiliation = {{Abaee, MS (Reprint Author), Chem \& Chem Engn Res Ctr Iran, POB 14335-186, Tehran, Iran. Abaee, M. Saeed; Mobayen, Fatemeh; Mojtahedi, Mohammad M.; Saberi, Farveh, Chem \& Chem Engn Res Ctr Iran, Tehran, Iran. Khavasi, Hamid Reza, Shahid Beheshti Univ, GC, Fac Chem, Tehran 1983963113, Iran.}}, author = {Abaee, M. Saeed and Mobayen, Fatemeh and Mojtahedi, Mohammad M. and Saberi, Farveh and Khavasi, Hamid Reza}, author-email = {{abaee@ccerci.ac.ir}}, biburl = {https://www.bibsonomy.org/bibtex/21f7a5e3cebfb44c144b008ba62014283/hkhavasi}, cited-references = {{Abaee MS, 2012, SYNLETT, P2073, DOI 10.1055/s-0031-1290438. Abaee MS, 2012, TETRAHEDRON LETT, V53, P4405, DOI 10.1016/j.tetlet.2012.06.040. Abaee MS, 2011, ACTA CHIM SLOV, V58, P605. Abaee MS, 2011, ORG LETT, V13, P5282, DOI 10.1021/ol202145w. Bella M, 2004, TETRAHEDRON, V60, P4821, DOI 10.1016/j.tet.2004.04.007. Bertozzi F, 2000, ORG LETT, V2, P1283, DOI 10.1021/ol0057232. Carmona D, 2014, J MOL CATAL A-CHEM, V385, P119, DOI 10.1016/j.molcata.2014.01.021. Didier D, 2012, SYNLETT, P1309, DOI 10.1055/s-0031-1290918. Fringuelli F., 2002, DIELS ALDER REACTION. Funel JA, 2013, ANGEW CHEM INT EDIT, V52, P3822, DOI 10.1002/anie.201201636. Han JC, 2013, J ORG CHEM, V78, P5492, DOI 10.1021/jo4006156. Heravi MM, 2015, RSC ADV, V5, P50890, DOI 10.1039/c5ra08306k. Hu HP, 2015, CHEM COMMUN, V51, P3835, DOI 10.1039/c4cc10343b. Ishihara J, 2015, J ORG CHEM, V80, P2037, DOI 10.1021/acs.joc.5b00055. Kang JM, 1998, J AM CHEM SOC, V120, P7389, DOI 10.1021/ja980927n. Kang TF, 2015, ADV SYNTH CATAL, V357, P2045, DOI 10.1002/adsc.201500069. Kobayashi M, 2011, ANGEW CHEM INT EDIT, V50, P1664, DOI 10.1002/anie.201004150. Mandal AB, 1997, J ORG CHEM, V62, P4105, DOI 10.1021/jo962403g. Mojtahedi MM, 2008, MONATSH CHEM, V139, P917, DOI 10.1007/s00706-007-0847-3. Mojtahedi MM, 2013, ULTRASON SONOCHEM, V20, P924, DOI 10.1016/j.ultsonch.2012.11.004. Phoenix S, 2008, J AM CHEM SOC, V130, P13989, DOI 10.1021/ja805097s. Samanta D, 2012, CHEM-EUR J, V18, P12322, DOI 10.1002/chem.201201679. Smith M. B., 2013, MARCHS ADV ORGANIC C, P1020.}}, doc-delivery-number = {{CX9MK}}, doi = {{10.3998/ark.5550190.p009.344}}, eissn = {{1551-7012}}, funding-acknowledgement = {{Iran National Science Foundation {[}INSF-92024196]}}, funding-text = {{Authors would like to thank Iran National Science Foundation (INSF-92024196) for financial support of this work.}}, interhash = {656eb74e557cf463db4b6d92fdad23e8}, intrahash = {1f7a5e3cebfb44c144b008ba62014283}, issn = {{1551-7004}}, journal = {{ARKIVOC}}, journal-iso = {{Arkivoc}}, keywords = {Diels-Alder aldol condensation; organocatalysis; reaction; stereoselectivity} {Tandem}, keywords-plus = {{DEHYDRODECALINE DERIVATIVES}}, language = {{English}}, number = {{7}}, number-of-cited-references = {{23}}, pages = {{305-315}}, publisher = {{ARKAT USA INC}}, research-areas = {{Chemistry}}, times-cited = {{3}}, timestamp = {2017-05-10T15:29:29.000+0200}, title = {{Et2NH/H2O catalyzed tandem aldol condensation - Diels-Alder cycloaddition sequence for the one-pot synthesis of (2R,3S)-rel-3-aryl-1,2,3,4,5,6,7,8-octahydro-6,6-dimethyl-8-oxo-2-naphth alenecarboxylates}}, type = {{Article}}, unique-id = {{ISI:000366029500024}}, usage-count-last-180-days = {{1}}, usage-count-since-2013 = {{2}}, web-of-science-categories = {{Chemistry, Organic}}, year = {{2015}} }