Practical Asymmetric Synthesis of α-Branched 2-Piperazinylbenzylamines by 1,2-Additions of Organometallic Reagents to N-tert-Butanesulfinyl Imines
2-[4-(tert-Butoxycarbonyl)piperazinyl]benzylidene-tert-butanesulfinamides underwent nucleophilic 1,2-addition with different organometallic reagents to give highly diastereomerically enriched adducts. X-ray crystallography of the resulting α-branched N-Boc-2-piperazinylbenzyl-tert-butanesulfinamides...
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| Veröffentlicht in: | Journal of organic chemistry 2005-10, Vol.70 (22), p.8924-8931 |
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| container_title | Journal of organic chemistry |
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| creator | Jiang, Wanlong Chen, Chen Marinkovic, Dragan Tran, Joe A Chen, Caroline W Arellano, L. Melissa White, Nicole S Tucci, Fabio C |
| description | 2-[4-(tert-Butoxycarbonyl)piperazinyl]benzylidene-tert-butanesulfinamides underwent nucleophilic 1,2-addition with different organometallic reagents to give highly diastereomerically enriched adducts. X-ray crystallography of the resulting α-branched N-Boc-2-piperazinylbenzyl-tert-butanesulfinamides confirms different mechanisms depending on the organometallic reagent used. Differential deprotection of the N-Boc and the tert-butanesulfinamides was investigated, and the dehydration byproducts have been identified and characterized. To avoid the formation of byproducts in the acidic deprotection step, the N-tert-butanesulfinamide group was converted to the corresponding N-tert-butanesulfonamide (Bus), which allowed for clean orthogonal deprotection. The efficient synthesis and deprotection of the N-Boc-2-piperazinylbenzyl-tert-butanesulfinamides herein described constitutes an attractive method for extensive structure−activity studies in the search for novel ligands of the human melanocortin 4 receptor. |
| doi_str_mv | 10.1021/jo051514p |
| format | Article |
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Melissa ; White, Nicole S ; Tucci, Fabio C</creator><creatorcontrib>Jiang, Wanlong ; Chen, Chen ; Marinkovic, Dragan ; Tran, Joe A ; Chen, Caroline W ; Arellano, L. Melissa ; White, Nicole S ; Tucci, Fabio C</creatorcontrib><description>2-[4-(tert-Butoxycarbonyl)piperazinyl]benzylidene-tert-butanesulfinamides underwent nucleophilic 1,2-addition with different organometallic reagents to give highly diastereomerically enriched adducts. X-ray crystallography of the resulting α-branched N-Boc-2-piperazinylbenzyl-tert-butanesulfinamides confirms different mechanisms depending on the organometallic reagent used. Differential deprotection of the N-Boc and the tert-butanesulfinamides was investigated, and the dehydration byproducts have been identified and characterized. To avoid the formation of byproducts in the acidic deprotection step, the N-tert-butanesulfinamide group was converted to the corresponding N-tert-butanesulfonamide (Bus), which allowed for clean orthogonal deprotection. The efficient synthesis and deprotection of the N-Boc-2-piperazinylbenzyl-tert-butanesulfinamides herein described constitutes an attractive method for extensive structure−activity studies in the search for novel ligands of the human melanocortin 4 receptor.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo051514p</identifier><identifier>PMID: 16238329</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Aldehydes - chemistry ; Alkylation ; Benzylamines - chemistry ; Butanes - chemistry ; Carbon - chemistry ; Catalysis ; Chemistry ; Crystallography, X-Ray ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Imines - chemical synthesis ; Imines - chemistry ; Kinetics and mechanisms ; Lithium - chemistry ; Molecular Structure ; Nitrogen - chemistry ; Organic chemistry ; Preparations and properties ; Reactivity and mechanisms ; Stereoisomerism ; Sulfur - chemistry</subject><ispartof>Journal of organic chemistry, 2005-10, Vol.70 (22), p.8924-8931</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a343t-bfd7a6bdba88dfedc08d7e44749e9708251bed87ae6e4140ccd0c9c2f63ec27d3</citedby><cites>FETCH-LOGICAL-a343t-bfd7a6bdba88dfedc08d7e44749e9708251bed87ae6e4140ccd0c9c2f63ec27d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo051514p$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo051514p$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17219614$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16238329$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jiang, Wanlong</creatorcontrib><creatorcontrib>Chen, Chen</creatorcontrib><creatorcontrib>Marinkovic, Dragan</creatorcontrib><creatorcontrib>Tran, Joe A</creatorcontrib><creatorcontrib>Chen, Caroline W</creatorcontrib><creatorcontrib>Arellano, L. Melissa</creatorcontrib><creatorcontrib>White, Nicole S</creatorcontrib><creatorcontrib>Tucci, Fabio C</creatorcontrib><title>Practical Asymmetric Synthesis of α-Branched 2-Piperazinylbenzylamines by 1,2-Additions of Organometallic Reagents to N-tert-Butanesulfinyl Imines</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>2-[4-(tert-Butoxycarbonyl)piperazinyl]benzylidene-tert-butanesulfinamides underwent nucleophilic 1,2-addition with different organometallic reagents to give highly diastereomerically enriched adducts. X-ray crystallography of the resulting α-branched N-Boc-2-piperazinylbenzyl-tert-butanesulfinamides confirms different mechanisms depending on the organometallic reagent used. Differential deprotection of the N-Boc and the tert-butanesulfinamides was investigated, and the dehydration byproducts have been identified and characterized. To avoid the formation of byproducts in the acidic deprotection step, the N-tert-butanesulfinamide group was converted to the corresponding N-tert-butanesulfonamide (Bus), which allowed for clean orthogonal deprotection. The efficient synthesis and deprotection of the N-Boc-2-piperazinylbenzyl-tert-butanesulfinamides herein described constitutes an attractive method for extensive structure−activity studies in the search for novel ligands of the human melanocortin 4 receptor.</description><subject>Aldehydes - chemistry</subject><subject>Alkylation</subject><subject>Benzylamines - chemistry</subject><subject>Butanes - chemistry</subject><subject>Carbon - chemistry</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Crystallography, X-Ray</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Imines - chemical synthesis</subject><subject>Imines - chemistry</subject><subject>Kinetics and mechanisms</subject><subject>Lithium - chemistry</subject><subject>Molecular Structure</subject><subject>Nitrogen - chemistry</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Reactivity and mechanisms</subject><subject>Stereoisomerism</subject><subject>Sulfur - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc9O3DAQhy1UBFvKgReofGmlSpjajhMnxwWVgoQA9c85cuwJGDnOYjuH8Bo8SV-kz1QvrNhL5zKXb74Z_QahI0ZPGOXs68NIS1YysdpBC1ZySqqGindoQSnnpOBVsY_ex_hAc5VluYf2WcWLuuDNAj3fBqWT1crhZZyHAVKwGv-cfbqHaCMee_z3DzkNyut7MJiTW7uCoJ6sn10H_ml2arAeIu5mzI45WRpjkx39y-RNuFN-zE7lXLb-AHUHPkWcRnxNEoRETqek8vTk-rUQX764PqDdXrkIh5t-gH6ff_t1dkGubr5fni2viCpEkUjXG6mqznSqrk0PRtPaSBBCigYaSWtesg5MLRVUIJigWhuqG837qgDNpSkO0OdX7yqMjxPE1A42anAunzROsa1qyRgrZQa_vII6jDEG6NtVsIMKc8tou_5A-_aBzH7cSKduALMlN5Fn4NMGUDHH3q-jtXHLSc6aioktp3TM_in4nMV_Fv4DmU6eEg</recordid><startdate>20051028</startdate><enddate>20051028</enddate><creator>Jiang, Wanlong</creator><creator>Chen, Chen</creator><creator>Marinkovic, Dragan</creator><creator>Tran, Joe A</creator><creator>Chen, Caroline W</creator><creator>Arellano, L. Melissa</creator><creator>White, Nicole S</creator><creator>Tucci, Fabio C</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20051028</creationdate><title>Practical Asymmetric Synthesis of α-Branched 2-Piperazinylbenzylamines by 1,2-Additions of Organometallic Reagents to N-tert-Butanesulfinyl Imines</title><author>Jiang, Wanlong ; Chen, Chen ; Marinkovic, Dragan ; Tran, Joe A ; Chen, Caroline W ; Arellano, L. Melissa ; White, Nicole S ; Tucci, Fabio C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a343t-bfd7a6bdba88dfedc08d7e44749e9708251bed87ae6e4140ccd0c9c2f63ec27d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Aldehydes - chemistry</topic><topic>Alkylation</topic><topic>Benzylamines - chemistry</topic><topic>Butanes - chemistry</topic><topic>Carbon - chemistry</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Crystallography, X-Ray</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Imines - chemical synthesis</topic><topic>Imines - chemistry</topic><topic>Kinetics and mechanisms</topic><topic>Lithium - chemistry</topic><topic>Molecular Structure</topic><topic>Nitrogen - chemistry</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Reactivity and mechanisms</topic><topic>Stereoisomerism</topic><topic>Sulfur - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jiang, Wanlong</creatorcontrib><creatorcontrib>Chen, Chen</creatorcontrib><creatorcontrib>Marinkovic, Dragan</creatorcontrib><creatorcontrib>Tran, Joe A</creatorcontrib><creatorcontrib>Chen, Caroline W</creatorcontrib><creatorcontrib>Arellano, L. Melissa</creatorcontrib><creatorcontrib>White, Nicole S</creatorcontrib><creatorcontrib>Tucci, Fabio C</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jiang, Wanlong</au><au>Chen, Chen</au><au>Marinkovic, Dragan</au><au>Tran, Joe A</au><au>Chen, Caroline W</au><au>Arellano, L. Melissa</au><au>White, Nicole S</au><au>Tucci, Fabio C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Practical Asymmetric Synthesis of α-Branched 2-Piperazinylbenzylamines by 1,2-Additions of Organometallic Reagents to N-tert-Butanesulfinyl Imines</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2005-10-28</date><risdate>2005</risdate><volume>70</volume><issue>22</issue><spage>8924</spage><epage>8931</epage><pages>8924-8931</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>2-[4-(tert-Butoxycarbonyl)piperazinyl]benzylidene-tert-butanesulfinamides underwent nucleophilic 1,2-addition with different organometallic reagents to give highly diastereomerically enriched adducts. X-ray crystallography of the resulting α-branched N-Boc-2-piperazinylbenzyl-tert-butanesulfinamides confirms different mechanisms depending on the organometallic reagent used. Differential deprotection of the N-Boc and the tert-butanesulfinamides was investigated, and the dehydration byproducts have been identified and characterized. To avoid the formation of byproducts in the acidic deprotection step, the N-tert-butanesulfinamide group was converted to the corresponding N-tert-butanesulfonamide (Bus), which allowed for clean orthogonal deprotection. The efficient synthesis and deprotection of the N-Boc-2-piperazinylbenzyl-tert-butanesulfinamides herein described constitutes an attractive method for extensive structure−activity studies in the search for novel ligands of the human melanocortin 4 receptor.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16238329</pmid><doi>10.1021/jo051514p</doi><tpages>8</tpages></addata></record> |
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| subjects | Aldehydes - chemistry Alkylation Benzylamines - chemistry Butanes - chemistry Carbon - chemistry Catalysis Chemistry Crystallography, X-Ray Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Imines - chemical synthesis Imines - chemistry Kinetics and mechanisms Lithium - chemistry Molecular Structure Nitrogen - chemistry Organic chemistry Preparations and properties Reactivity and mechanisms Stereoisomerism Sulfur - chemistry |
| title | Practical Asymmetric Synthesis of α-Branched 2-Piperazinylbenzylamines by 1,2-Additions of Organometallic Reagents to N-tert-Butanesulfinyl Imines |
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