Mapping the Active Site in a Chemzyme: Diversity in the N-Substituent in the Catalytic Asymmetric Aziridination of Imines
The active site of the aziridination catalyst derived from either the VANOL or VAPOL ligand and B(OPh)3 is larger than expected and can accommodate not only significant substitution on the diarylmethyl unit of the imine but also that alkyl (but not perfluorylalkyl) substituents on the aryl groups le...
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| Veröffentlicht in: | Organic letters 2008-12, Vol.10 (23), p.5429-5432 |
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| container_title | Organic letters |
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| creator | Zhang, Yu Lu, Zhenjie Desai, Aman Wulff, William D |
| description | The active site of the aziridination catalyst derived from either the VANOL or VAPOL ligand and B(OPh)3 is larger than expected and can accommodate not only significant substitution on the diarylmethyl unit of the imine but also that alkyl (but not perfluorylalkyl) substituents on the aryl groups lead to enhanced rates and enantioselection. The screen of diarylmethyl N-substituents on the imine revealed that the 3,5-di-tert-butyldianisylmethyl group (BUDAM) gave exceptionally high asymmetric inductions for imines of aryl aldehydes. |
| doi_str_mv | 10.1021/ol802431v |
| format | Article |
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The screen of diarylmethyl N-substituents on the imine revealed that the 3,5-di-tert-butyldianisylmethyl group (BUDAM) gave exceptionally high asymmetric inductions for imines of aryl aldehydes.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol802431v</identifier><identifier>PMID: 18989967</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Aziridines - chemistry ; Catalysis ; Catalytic Domain ; Electrons ; Imines - chemistry ; Molecular Conformation ; Naphthalenes - chemistry ; Nitrogen - chemistry</subject><ispartof>Organic letters, 2008-12, Vol.10 (23), p.5429-5432</ispartof><rights>Copyright © 2008 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a415t-ad1b6dc56451d23ce7e90049a60626ed93ba7cf90dcf0942edf11ca02743e1503</citedby><cites>FETCH-LOGICAL-a415t-ad1b6dc56451d23ce7e90049a60626ed93ba7cf90dcf0942edf11ca02743e1503</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/ol802431v$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol802431v$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18989967$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Yu</creatorcontrib><creatorcontrib>Lu, Zhenjie</creatorcontrib><creatorcontrib>Desai, Aman</creatorcontrib><creatorcontrib>Wulff, William D</creatorcontrib><title>Mapping the Active Site in a Chemzyme: Diversity in the N-Substituent in the Catalytic Asymmetric Aziridination of Imines</title><title>Organic letters</title><addtitle>Org. 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The screen of diarylmethyl N-substituents on the imine revealed that the 3,5-di-tert-butyldianisylmethyl group (BUDAM) gave exceptionally high asymmetric inductions for imines of aryl aldehydes.</description><subject>Aziridines - chemistry</subject><subject>Catalysis</subject><subject>Catalytic Domain</subject><subject>Electrons</subject><subject>Imines - chemistry</subject><subject>Molecular Conformation</subject><subject>Naphthalenes - chemistry</subject><subject>Nitrogen - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtOwzAURC0EoqWw4AeQNwixCNhxHjW7KjylAovCOnKcG-oqToLtVEq_nkQtZcPqjmaORrqD0DklN5T49LYup8QPGF0foDENfebFJPQP9zoiI3Ri7YoQ2jv8GI3olE85j-Ix6l5F06jqC7sl4Jl0ag14oRxgVWGBkyXoTafhDt_3gbHKdUMwsG_eos2sU66Fyv2aiXCi7JySeGY7rcGZQW6UUbmqhFN1hesCv2hVgT1FR4UoLZzt7gR9Pj58JM_e_P3pJZnNPRHQ0Hkip1mUyzAKQpr7TEIMnJCAi4hEfgQ5Z5mIZcFJLgvCAx_yglIpiB8HDGhI2ARdbXsbU3-3YF2qlZVQlqKCurVpzFgQ0CmNevJ6S0pTW2ugSBujtDBdSkk6DJ3uh-7Zi11rm2nI_8jdsj1wuQWEtOmqbk3VP_lP0Q8iH4WE</recordid><startdate>20081204</startdate><enddate>20081204</enddate><creator>Zhang, Yu</creator><creator>Lu, Zhenjie</creator><creator>Desai, Aman</creator><creator>Wulff, William D</creator><general>American Chemical Society</general><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>20081204</creationdate><title>Mapping the Active Site in a Chemzyme: Diversity in the N-Substituent in the Catalytic Asymmetric Aziridination of Imines</title><author>Zhang, Yu ; Lu, Zhenjie ; Desai, Aman ; Wulff, William D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a415t-ad1b6dc56451d23ce7e90049a60626ed93ba7cf90dcf0942edf11ca02743e1503</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Aziridines - chemistry</topic><topic>Catalysis</topic><topic>Catalytic Domain</topic><topic>Electrons</topic><topic>Imines - chemistry</topic><topic>Molecular Conformation</topic><topic>Naphthalenes - chemistry</topic><topic>Nitrogen - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Yu</creatorcontrib><creatorcontrib>Lu, Zhenjie</creatorcontrib><creatorcontrib>Desai, Aman</creatorcontrib><creatorcontrib>Wulff, William D</creatorcontrib><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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Yu</au><au>Lu, Zhenjie</au><au>Desai, Aman</au><au>Wulff, William D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Mapping the Active Site in a Chemzyme: Diversity in the N-Substituent in the Catalytic Asymmetric Aziridination of Imines</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2008-12-04</date><risdate>2008</risdate><volume>10</volume><issue>23</issue><spage>5429</spage><epage>5432</epage><pages>5429-5432</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The active site of the aziridination catalyst derived from either the VANOL or VAPOL ligand and B(OPh)3 is larger than expected and can accommodate not only significant substitution on the diarylmethyl unit of the imine but also that alkyl (but not perfluorylalkyl) substituents on the aryl groups lead to enhanced rates and enantioselection. The screen of diarylmethyl N-substituents on the imine revealed that the 3,5-di-tert-butyldianisylmethyl group (BUDAM) gave exceptionally high asymmetric inductions for imines of aryl aldehydes.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>18989967</pmid><doi>10.1021/ol802431v</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2008-12, Vol.10 (23), p.5429-5432 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Aziridines - chemistry Catalysis Catalytic Domain Electrons Imines - chemistry Molecular Conformation Naphthalenes - chemistry Nitrogen - chemistry |
| title | Mapping the Active Site in a Chemzyme: Diversity in the N-Substituent in the Catalytic Asymmetric Aziridination of Imines |
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