<?xml version="1.0" encoding="ISO-8859-1"?><article xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance">
<front>
<journal-meta>
<journal-id>1870-249X</journal-id>
<journal-title><![CDATA[Journal of the Mexican Chemical Society]]></journal-title>
<abbrev-journal-title><![CDATA[J. Mex. Chem. Soc]]></abbrev-journal-title>
<issn>1870-249X</issn>
<publisher>
<publisher-name><![CDATA[Sociedad Química de México A.C.]]></publisher-name>
</publisher>
</journal-meta>
<article-meta>
<article-id>S1870-249X2024000100144</article-id>
<article-id pub-id-type="doi">10.29356/jmcs.v68i1.2067</article-id>
<title-group>
<article-title xml:lang="en"><![CDATA[4(S)-Benzyl-1,3-thiazolidin-2-one a Novel Chiral Auxiliary for Asymmetric Aldol Coupling through Titanium Enolates]]></article-title>
<article-title xml:lang="es"><![CDATA[4(S)-bencil-1,3-tiazolidin-2-ona: un nuevo auxiliar quiral para el acoplamiento aldólico asimétrico a través de enolatos de titanio]]></article-title>
</title-group>
<contrib-group>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Mejía-Nuñez]]></surname>
<given-names><![CDATA[Dulce M.]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Mastachi-Loza]]></surname>
<given-names><![CDATA[Salvador]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Martínez-Otero]]></surname>
<given-names><![CDATA[Diego]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Romero-Ortega]]></surname>
<given-names><![CDATA[Moisés]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
</contrib-group>
<aff id="Af1">
<institution><![CDATA[,Universidad Autónoma del Estado de México Facultad de Química Departamento de Química Orgánica]]></institution>
<addr-line><![CDATA[Toluca ]]></addr-line>
<country>Mexico</country>
</aff>
<aff id="Af2">
<institution><![CDATA[,Universidad Nacional Autónoma de México Instituto de Química Centro Conjunto de Investigación en Química Sustentable]]></institution>
<addr-line><![CDATA[Toluca ]]></addr-line>
<country>Mexico</country>
</aff>
<pub-date pub-type="pub">
<day>00</day>
<month>03</month>
<year>2024</year>
</pub-date>
<pub-date pub-type="epub">
<day>00</day>
<month>03</month>
<year>2024</year>
</pub-date>
<volume>68</volume>
<numero>1</numero>
<fpage>144</fpage>
<lpage>155</lpage>
<copyright-statement/>
<copyright-year/>
<self-uri xlink:href="http://www.scielo.org.mx/scielo.php?script=sci_arttext&amp;pid=S1870-249X2024000100144&amp;lng=en&amp;nrm=iso"></self-uri><self-uri xlink:href="http://www.scielo.org.mx/scielo.php?script=sci_abstract&amp;pid=S1870-249X2024000100144&amp;lng=en&amp;nrm=iso"></self-uri><self-uri xlink:href="http://www.scielo.org.mx/scielo.php?script=sci_pdf&amp;pid=S1870-249X2024000100144&amp;lng=en&amp;nrm=iso"></self-uri><abstract abstract-type="short" xml:lang="en"><p><![CDATA[Abstract. The chlorotitanium enolate of N-propionyl-4(S)-benzyl-1,3-thiazolidin-2-one, was condensed with aryl aldehydes, in good diastereoselectivity to give the &#8216;Evans syn&#8217; aldol (73:27 - 97:3), using equimolar amounts of titanium tetrachloride (1.5 equiv), and N,N-diisopropylethylamine (DIPEA). The facial selectivity in the aldol additions probably involves a non-chelated transition state. In all aldol reactions, the presence of a minor product, the &#8216;non-Evans syn&#8217; aldol, was obtained and confirmed by X-ray diffraction analysis of a single-crystal compound containing the mixture of diastereoisomers. The chiral auxiliary in these 1,3-thiazolidin-2-one aldol derivatives can be easily removed by nucleophilic species through acyl substitution.]]></p></abstract>
<abstract abstract-type="short" xml:lang="es"><p><![CDATA[Resumen. El enolato de clorotitanio de N-propionil-4(S)-bencil-1,3-tiazolidin-2-ona, fue condensado con arilaldehídos, con buena diastereoselectividad produciendo el aldol &#8220;syn Evans&#8221; (73:27 - 97:3), utilizando cantidades equimolares de tetracloruro de titanio (1.5 equiv) y N,N-diisopropiletilamina (DIPEA). La selectividad facial en las adiciones aldólicas probablemente implica un estado de transición no-quelatado. En todas las reacciones aldólicas, la presencia de un producto minoritario, él aldol &#8220;non-Evans&#8221;, fue obtenido y confirmado por el análisis de difracción de rayos-X de monocristal de una mezcla de los diastereoisómeros. El auxiliar quiral en estos derivados de 1,3-tiazolidin-2-onas puede ser removido fácilmente por especies nucleofílicas a través de la sustitución del grupo acilo.]]></p></abstract>
<kwd-group>
<kwd lng="en"><![CDATA[Chiral auxiliaries]]></kwd>
<kwd lng="en"><![CDATA[coupling reaction]]></kwd>
<kwd lng="en"><![CDATA[stereoselective synthesis]]></kwd>
<kwd lng="en"><![CDATA[aldol adducts]]></kwd>
<kwd lng="en"><![CDATA[thiazolidinone]]></kwd>
<kwd lng="es"><![CDATA[Auxiliar quiral]]></kwd>
<kwd lng="es"><![CDATA[reacción de acoplamiento]]></kwd>
<kwd lng="es"><![CDATA[síntesis estereoselectiva]]></kwd>
<kwd lng="es"><![CDATA[aductos aldolicos]]></kwd>
<kwd lng="es"><![CDATA[tiazolidinona]]></kwd>
</kwd-group>
</article-meta>
</front><back>
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