Highly efficient, multigram and enantiopure synthesis of ( S)-2-(2,4′-bithiazol-2-yl)pyrrolidine
( S)-2-(4-Bromo-2,4′-bithiazole)-1-( tert-butoxycarbonyl)pyrrolidine ( ( S )- 1) was obtained as a single enantiomer and in high yield by means of a two-step modified Hantzsch thiazole synthesis reaction when bromoketone 3 and thioamide ( S )- 4 were used. Further conversion of ( S )- 1 into trimeth...
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| Veröffentlicht in: | Tetrahedron letters 2011-10, Vol.52 (42), p.5435-5437 |
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| container_title | Tetrahedron letters |
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| creator | Just-Baringo, Xavier Bruno, Paolo Albericio, Fernando Álvarez, Mercedes |
| description | (
S)-2-(4-Bromo-2,4′-bithiazole)-1-(
tert-butoxycarbonyl)pyrrolidine (
(
S
)-
1) was obtained as a single enantiomer and in high yield by means of a two-step modified Hantzsch thiazole synthesis reaction when bromoketone
3 and thioamide
(
S
)-
4 were used. Further conversion of
(
S
)-
1 into trimethyltin derivative
(
S
)-
2 broadens the scope for further cross-coupling reactions. |
| doi_str_mv | 10.1016/j.tetlet.2011.07.128 |
| format | Article |
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S)-2-(4-Bromo-2,4′-bithiazole)-1-(
tert-butoxycarbonyl)pyrrolidine (
(
S
)-
1) was obtained as a single enantiomer and in high yield by means of a two-step modified Hantzsch thiazole synthesis reaction when bromoketone
3 and thioamide
(
S
)-
4 were used. Further conversion of
(
S
)-
1 into trimethyltin derivative
(
S
)-
2 broadens the scope for further cross-coupling reactions.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2011.07.128</identifier><identifier>CODEN: TELEAY</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>Antibiotics ; Antibiòtics ; Chemical reactions ; Chemistry ; Compostos heterocíclics ; Conversion ; Derivatives ; Enantiomers ; Enantiòmers ; Exact sciences and technology ; Hantzsch cyclization ; Heterocyclic compounds ; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Natural products ; Organic chemistry ; Peptide synthesis ; Preparations and properties ; Productes naturals ; Proline ; Synthesis (chemistry) ; Síntesi de pèptids ; Tetrahedrons ; Thiazole ; Thiopeptides</subject><ispartof>Tetrahedron letters, 2011-10, Vol.52 (42), p.5435-5437</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>(c) Elsevier Ltd, 2011 info:eu-repo/semantics/openAccess</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c457t-8d53d62ba057847caf56a88b50f5782efd2f2ac69978fdd9ef93a754c5c85da13</citedby><cites>FETCH-LOGICAL-c457t-8d53d62ba057847caf56a88b50f5782efd2f2ac69978fdd9ef93a754c5c85da13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tetlet.2011.07.128$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,777,781,882,3537,26955,27905,27906,45976</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24540431$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Just-Baringo, Xavier</creatorcontrib><creatorcontrib>Bruno, Paolo</creatorcontrib><creatorcontrib>Albericio, Fernando</creatorcontrib><creatorcontrib>Álvarez, Mercedes</creatorcontrib><title>Highly efficient, multigram and enantiopure synthesis of ( S)-2-(2,4′-bithiazol-2-yl)pyrrolidine</title><title>Tetrahedron letters</title><description>(
S)-2-(4-Bromo-2,4′-bithiazole)-1-(
tert-butoxycarbonyl)pyrrolidine (
(
S
)-
1) was obtained as a single enantiomer and in high yield by means of a two-step modified Hantzsch thiazole synthesis reaction when bromoketone
3 and thioamide
(
S
)-
4 were used. Further conversion of
(
S
)-
1 into trimethyltin derivative
(
S
)-
2 broadens the scope for further cross-coupling reactions.</description><subject>Antibiotics</subject><subject>Antibiòtics</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>Compostos heterocíclics</subject><subject>Conversion</subject><subject>Derivatives</subject><subject>Enantiomers</subject><subject>Enantiòmers</subject><subject>Exact sciences and technology</subject><subject>Hantzsch cyclization</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Natural products</subject><subject>Organic chemistry</subject><subject>Peptide synthesis</subject><subject>Preparations and properties</subject><subject>Productes naturals</subject><subject>Proline</subject><subject>Synthesis (chemistry)</subject><subject>Síntesi de pèptids</subject><subject>Tetrahedrons</subject><subject>Thiazole</subject><subject>Thiopeptides</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>XX2</sourceid><recordid>eNp9kc2KFDEQxxtRcFx9Aw99EWZhu81nJ30RZFFXWPCgnkMmqexkyHTGJC20J5_JR_JJTDOD3iwoiirqX1XUr2leYtRjhIfXh75ACVB6gjDukegxkY-aDZaCdpRL_LjZIMRQxxAdnzbPcj6gaoNEm2Z35x_2YWnBOW88TOWmPc6h-Iekj62ebAuTnoqPpzlBm5ep7CH73EbXbtvP1x3ptuSG_f75q9v5svf6Rwy1toTr05JSDN76CZ43T5wOGV5c4lXz9f27L7d33f2nDx9v3953hnFROmk5tQPZacSFZMJoxwct5Y4jVwsEnCWOaDOMo5DO2hHcSLXgzHAjudWYXjX4PNfk2agEBpLRRUXt_yWrEySIIpQiOVTN9qw5pfhthlzU0WcDIegJ4pwVFowJxIgYayu7jE8x5wROnZI_6rQojNSKQR3UGYNaMSgkVMVQZa8uG3Q2OrikJ-PzXy1hnCFG1-vfnPugvui7h6TyysOA9fX6omz0_1_0BxGUoA8</recordid><startdate>20111019</startdate><enddate>20111019</enddate><creator>Just-Baringo, Xavier</creator><creator>Bruno, Paolo</creator><creator>Albericio, Fernando</creator><creator>Álvarez, Mercedes</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>XX2</scope></search><sort><creationdate>20111019</creationdate><title>Highly efficient, multigram and enantiopure synthesis of ( S)-2-(2,4′-bithiazol-2-yl)pyrrolidine</title><author>Just-Baringo, Xavier ; Bruno, Paolo ; Albericio, Fernando ; Álvarez, Mercedes</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c457t-8d53d62ba057847caf56a88b50f5782efd2f2ac69978fdd9ef93a754c5c85da13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Antibiotics</topic><topic>Antibiòtics</topic><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>Compostos heterocíclics</topic><topic>Conversion</topic><topic>Derivatives</topic><topic>Enantiomers</topic><topic>Enantiòmers</topic><topic>Exact sciences and technology</topic><topic>Hantzsch cyclization</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Natural products</topic><topic>Organic chemistry</topic><topic>Peptide synthesis</topic><topic>Preparations and properties</topic><topic>Productes naturals</topic><topic>Proline</topic><topic>Synthesis (chemistry)</topic><topic>Síntesi de pèptids</topic><topic>Tetrahedrons</topic><topic>Thiazole</topic><topic>Thiopeptides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Just-Baringo, Xavier</creatorcontrib><creatorcontrib>Bruno, Paolo</creatorcontrib><creatorcontrib>Albericio, Fernando</creatorcontrib><creatorcontrib>Álvarez, Mercedes</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Recercat</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Just-Baringo, Xavier</au><au>Bruno, Paolo</au><au>Albericio, Fernando</au><au>Álvarez, Mercedes</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly efficient, multigram and enantiopure synthesis of ( S)-2-(2,4′-bithiazol-2-yl)pyrrolidine</atitle><jtitle>Tetrahedron letters</jtitle><date>2011-10-19</date><risdate>2011</risdate><volume>52</volume><issue>42</issue><spage>5435</spage><epage>5437</epage><pages>5435-5437</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><coden>TELEAY</coden><abstract>(
S)-2-(4-Bromo-2,4′-bithiazole)-1-(
tert-butoxycarbonyl)pyrrolidine (
(
S
)-
1) was obtained as a single enantiomer and in high yield by means of a two-step modified Hantzsch thiazole synthesis reaction when bromoketone
3 and thioamide
(
S
)-
4 were used. Further conversion of
(
S
)-
1 into trimethyltin derivative
(
S
)-
2 broadens the scope for further cross-coupling reactions.</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2011.07.128</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record> |
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| source | Elsevier ScienceDirect Journals; Recercat |
| subjects | Antibiotics Antibiòtics Chemical reactions Chemistry Compostos heterocíclics Conversion Derivatives Enantiomers Enantiòmers Exact sciences and technology Hantzsch cyclization Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Heterocyclic compounds with only one n hetero atom and condensed derivatives Natural products Organic chemistry Peptide synthesis Preparations and properties Productes naturals Proline Synthesis (chemistry) Síntesi de pèptids Tetrahedrons Thiazole Thiopeptides |
| title | Highly efficient, multigram and enantiopure synthesis of ( S)-2-(2,4′-bithiazol-2-yl)pyrrolidine |
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