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Enantioselective addition of diethylzinc to aldehydes catalyzed by gamma-amino alcohols derived from (+)- and (-)-alpha-pinene
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Primary, secondary and tertiary gamma-amino alcohols 4, 5, 7 and 9 and 1,3-diamine 6 were synthesized from (+)- and (-)-alpha-pinene 1 via chiral N-Boc beta-amino ester 3a and carboxamide 3b. The amino alcohols and diamine obtained were applied as chiral catalysts in the enantioselective addition of diethylzinc to aromatic aldehydes, resulting in chiral 1-aryl-1-propanols. The first evidence of the substituent-dependent enantioselectivity of 1,3-amino alcohol catalysts was observed, and the phenomenon interpreted by using molecular modelling at the ab initio level. (c) 2005 Elsevier Ltd. All rights reserved.
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<div class="JournalArticle Publication short-list"> <div class="authors"> <span class="author-name" mtid="10002784"> <a href="/gui2/?type=authors&mode=browse&sel=10002784" target="_blank">Szakonyi, Z</a> </span> <span class="author-type"> </span> ; <span class="author-name" > Balazs, A </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10001168"> <a href="/gui2/?type=authors&mode=browse&sel=10001168" target="_blank">Martinek, T A</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="1381350"> <a href="/gui2/?type=authors&mode=browse&sel=1381350" target="_blank">Fulop, F</a> </span> <span class="author-type"> </span> </div ><div class="title"><a href="/gui2/?mode=browse¶ms=publication;1012940" mtid="1012940" target="_blank">Enantioselective addition of diethylzinc to aldehydes catalyzed by gamma-amino alcohols derived from (+)- and (-)-alpha-pinene</a></div> <div class="pub-info"> <span class="journal-title">TETRAHEDRON-ASYMMETRY</span> <span class="journal-volume">17</span> : <span class="journal-issue">2</span> <span class="page"> pp. 199-204. , 6 p. </span> <span class="year">(2006)</span> </div> <div class="pub-end"><div class="identifier-list"> <span class="identifiers"> <span class="id identifier oa_PAY" title=" Fizetős "> <a style="color:blue" title="10.1016/j.tetasy.2005.12.011" target="_blank" href="https://doi.org/10.1016/j.tetasy.2005.12.011"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="S0957416605009924" target="_blank" href="http://www.sciencedirect.com/science/article/pii/S0957416605009924"> ScienceDirect </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="000235579500007" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/000235579500007"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="32444447241" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-32444447241"> Scopus </a> </span> </span> </div> <div class="short-pub-prop-list"> <span class="short-pub-mtid"> Közlemény:1012940 </span> <span class="status-holder"><span class="status-data status-VALIDATED"> Egyeztetett </span></span> <span class="pub-core">Forrás Idéző </span> <span class="pub-type">Folyóiratcikk (Szakcikk ) </span> <!-- && !record.category.scientific --> <span class="pub-category">Tudományos</span> <div class="publication-citation" style="margin-left: 0.5cm;"> <span title="Nyilvános idézőközlemények összesen, említések nélkül" class="citingPub-count">Nyilvános idéző összesen: 81</span> | Független: 50 | Függő: 31 | Nem jelölt: 0 | WoS jelölt: 72 | Scopus jelölt: 76 | WoS/Scopus jelölt: 78 | DOI jelölt: 76 </div> <div class="publication-citation" style="margin-left: 0.5cm; margin-top:0"> <span title="Nyilvános idézéskapcsolatok száma (egy közleményen belüli többszörös említésekkel együtt)" class="citingPub-count">Nyilvános idéző+említés összesen: 82</span> | Független: 50 | Függő: 32 | Nem jelölt: 0 </div> </div> </div> </div><div class="JournalArticle Publication long-list">
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<div class="title"><a href="/gui2/?mode=browse¶ms=publication;1012940" target="_blank">Enantioselective addition of diethylzinc to aldehydes catalyzed by gamma-amino alcohols derived from (+)- and (-)-alpha-pinene</a></div> <div> <span class="journal-title">TETRAHEDRON-ASYMMETRY</span>
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<span title="Nyilvános idézőközlemények összesen, említések nélkül" class="citingPub-count">Nyilvános idéző összesen: 81</span>
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<div class="lastModified">Utolsó módosítás: 2023.09.06. 15:06 Hetényi Anasztázia (SZTE ÁOK admin5 Orvosi Vegytani Intézet)
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<pre class="comment" style="margin-top: 0; margin-bottom: 0;"><u>Megjegyzés</u>: CAplus AN 2006:128546 (Journal);</pre>
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Correspondence Address: Fülöp, F.; Inst. of Pharmaceutical Chemistry, POB 121, H-6701 Szeged, Hungary; email: fulop@pharma.szote.u-szeged.hu
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Regio- and stereospecific addition of chlorosulfonyl isocyanate
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pure beta -lactams 2, which were converted to enantiomeric beta
-amino esters 3 and 1,3-amino alcohols 4 and 6 with ee >99%. The
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<div class="JournalArticle Publication short-list"> <div class="authors"> <span class="author-name" mtid="10002784"> <a href="/gui2/?type=authors&mode=browse&sel=10002784" target="_blank">Szakonyi, Z</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10001168"> <a href="/gui2/?type=authors&mode=browse&sel=10001168" target="_blank">Martinek, T</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10001147"> <a href="/gui2/?type=authors&mode=browse&sel=10001147" target="_blank">Hetenyi, A</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="1381350"> <a href="/gui2/?type=authors&mode=browse&sel=1381350" target="_blank">Fulop, F</a> </span> <span class="author-type"> </span> </div ><div class="title"><a href="/gui2/?mode=browse¶ms=publication;1014481" mtid="1014481" target="_blank">Synthesis and transformations of enantiomeric 1,2-disubstituted monoterpene derivatives</a></div> <div class="pub-info"> <span class="journal-title">TETRAHEDRON-ASYMMETRY</span> <span class="journal-volume">11</span> : <span class="journal-issue">22</span> <span class="page"> pp. 4571-4579. , 9 p. </span> <span class="year">(2000)</span> </div> <div class="pub-end"><div class="identifier-list"> <span class="identifiers"> <span class="id identifier oa_PAY" title=" Fizetős "> <a style="color:blue" title="10.1016/S0957-4166(00)00435-3" target="_blank" href="https://doi.org/10.1016/S0957-4166%2800%2900435-3"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="S0957416600004353" target="_blank" href="http://www.sciencedirect.com/science/article/pii/S0957416600004353"> ScienceDirect </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="000166140800018" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/000166140800018"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="0034680469" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-0034680469"> Scopus </a> </span> </span> </div> <div class="short-pub-prop-list"> <span class="short-pub-mtid"> Közlemény:1014481 </span> <span class="status-holder"><span class="status-data status-VALIDATED"> Egyeztetett </span></span> <span class="pub-core">Forrás Idéző </span> <span class="pub-type">Folyóiratcikk (Szakcikk ) </span> <!-- && !record.category.scientific --> <span class="pub-category">Tudományos</span> <div class="publication-citation" style="margin-left: 0.5cm;"> <span title="Nyilvános idézőközlemények összesen, említések nélkül" class="citingPub-count">Nyilvános idéző összesen: 62</span> | Független: 29 | Függő: 33 | Nem jelölt: 0 | WoS jelölt: 49 | Scopus jelölt: 51 | WoS/Scopus jelölt: 52 | DOI jelölt: 50 </div> </div> </div> </div><div class="JournalArticle Publication long-list">
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<span class="authorAux-mtmt"> szerves- és gyógyszerkémia</span>)
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<span class="author-affil"><span title="Szegedi Tudományegyetem">SZTE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/Gyógyszerkémiai Intézet</span>
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<span class="author-name" mtid="10001147"><a
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<span class="authorAux-mtmt"> NMR spektroszkópia, molekulamodellezés</span>)
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</span>
<span class="author-affil"><span title="Szegedi Tudományegyetem">SZTE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/Gyógyszerkémiai Intézet</span>
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<span class="author-affil"><span title="Szegedi Tudományegyetem">SZTE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/Gyógyszerkémiai Intézet</span>
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<div class="title"><a href="/gui2/?mode=browse¶ms=publication;1014481" target="_blank">Synthesis and transformations of enantiomeric 1,2-disubstituted monoterpene derivatives</a></div> <div> <span class="journal-title">TETRAHEDRON-ASYMMETRY</span>
<span class="journal-issn">(<a target="_blank" href="https://portal.issn.org/resource/ISSN/0957-4166">0957-4166</a> <a target="_blank" href="https://portal.issn.org/resource/ISSN/1362-511X">1362-511X</a>)</span>:
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ScienceDirect
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<span title="Nyilvános idézőközlemények összesen, említések nélkül" class="citingPub-count">Nyilvános idéző összesen: 62</span>
| Független: 29
| Függő: 33
| Nem jelölt: 0
| WoS jelölt: 49
| Scopus jelölt: 51
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<div class="lastModified">Utolsó módosítás: 2020.12.17. 09:28 Szuper Admin (admin)
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<pre class="comment" style="margin-top: 0; margin-bottom: 0;"><u>Megjegyzés</u>: Cited By :50
Export Date: 8 September 2023
CODEN: TASYE
Correspondence Address: Fülöp, F.; Inst. of Pharmaceutical Chemistry, POB 121, H-6701 Szeged, Hungary; email: fulop@pharma.szote.u-szeged.hu</pre>
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The formation of perhydro-1,3-oxazine derivatives (3) through the cyclization reaction of p-nitrobenzaldehyde with cis- (1) and trans-2-aminomethyl-1-cyclohexanol (2) or with their N-methyl derivatives (1m and 2m) were studied by H-1 NMR spectroscopy in CDCl3. The reactions with 1 and 2 proceeded via open-chain intermediates whereas those with 1m and 2m showed no signs of these intermediates. The cyclization reactions of the N-methyl substituted cyclohexanols (1m and 2m) were much faster than those of the corresponding hydroxymethylcyclohexylamines studied earlier. The cyclization of 1 was kinetically controlled but in much lesser extent than the corresponding reaction with cis-2-hydroxymethyl-1-cyclohexylamine. These results confirmed that the cyclization reactions of p-nitrobenzaldehyde with 2-aminomethyl-1-cyclohexanols and their N-methyl derivatives parallel to those with 2-hydroxymethyl-1-cyclohexylamines and their N-methyl derivatives are not usually diastereospecific.
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<div class="JournalArticle Publication short-list"> <div class="authors"> <span class="author-name" > Parkkinen, A </span> <span class="author-type"> </span> ; <span class="author-name" mtid="1381350"> <a href="/gui2/?type=authors&mode=browse&sel=1381350" target="_blank">Fulop, F</a> </span> <span class="author-type"> </span> ; <span class="author-name" > Pihlaja, K </span> <span class="author-type"> </span> </div ><div class="title"><a href="/gui2/?mode=browse¶ms=publication;1016222" mtid="1016222" target="_blank">FORMATION OF 1,3-PERHYDROBENZOXAZINES AND THEIR N-METHYL DERIVATIVES - A COMPARATIVE-STUDY</a></div> <div class="pub-info"> <span class="journal-title">TETRAHEDRON</span> <span class="journal-volume">47</span> : <span class="journal-issue">12-13</span> <span class="page"> pp. 2229-2236. , 8 p. </span> <span class="year">(1991)</span> </div> <div class="pub-end"><div class="identifier-list"> <span class="identifiers"> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="10.1016/S0040-4020(01)96133-2" target="_blank" href="https://doi.org/10.1016/S0040-4020%2801%2996133-2"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:black" title="S0040402001961332" target="_blank" href="http://www.sciencedirect.com/science/article/pii/S0040402001961332"> ScienceDirect </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="A1991FB16300018" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/A1991FB16300018"> WoS </a> </span> </span> </div> <div class="short-pub-prop-list"> <span class="short-pub-mtid"> Közlemény:1016222 </span> <span class="status-holder"><span class="status-data status-APPROVED"> Nyilvános </span></span> <span class="pub-core">Forrás Idéző </span> <span class="pub-type">Folyóiratcikk (Szakcikk ) </span> <!-- && !record.category.scientific --> <span class="pub-category">Tudományos</span> <div class="publication-citation" style="margin-left: 0.5cm;"> <span title="Nyilvános idézőközlemények összesen, említések nélkül" class="citingPub-count">Nyilvános idéző összesen: 9</span> | Független: 4 | Függő: 5 | Nem jelölt: 0 | WoS jelölt: 8 | Scopus jelölt: 6 | WoS/Scopus jelölt: 8 | DOI jelölt: 6 </div> </div> </div> </div><div class="JournalArticle Publication long-list"> <div class="authors"> <img title="Forrásközlemény" style="float: left" src="/frontend/resources/grid/publication-core-icon.png"> <img title="Idézőközlemény" style="float: left" src="/frontend/resources/grid/publication-citation-icon.png"> <div class="autype autype0"> <span class="author-name" >Parkkinen A </span> ; 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