Design and Synthesis of Planar Chiral Heterocyclic Carbene Precursors Derived from [2.2]Paracyclophane
A unique family of planar chiral symmetrical N-heterocyclic carbene precursors with restricted flexibility derived from [2.2]paracyclopane were obtained by a new synthetic route. The resolution of 4-amino-13-bromo[2.2]paracyclophane was achieved with relatively high efficiency. Starting from (4S p,1...
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| Veröffentlicht in: | Journal of organic chemistry 2008-06, Vol.73 (11), p.4330-4333 |
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| container_end_page | 4333 |
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| container_issue | 11 |
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| container_title | Journal of organic chemistry |
| container_volume | 73 |
| creator | Duan, Wenzeng Ma, Yudao Xia, Houqi Liu, Xueying Ma, Qingshuang Sun, Junshan |
| description | A unique family of planar chiral symmetrical N-heterocyclic carbene precursors with restricted flexibility derived from [2.2]paracyclopane were obtained by a new synthetic route. The resolution of 4-amino-13-bromo[2.2]paracyclophane was achieved with relatively high efficiency. Starting from (4S p,13R p)-4-amino-13-bromo[2.2]paracyclophane, the planar chiral pseudogem-disubstituted [2.2]paracyclophanyl dihydroimidazoliums were prepared in a four-step sequence with good yields. The resulting dihydroimidazolium salts were fully characterized with a series of methods including single-crystal X-ray diffraction technique. |
| doi_str_mv | 10.1021/jo800468x |
| format | Article |
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Org. Chem</addtitle><description>A unique family of planar chiral symmetrical N-heterocyclic carbene precursors with restricted flexibility derived from [2.2]paracyclopane were obtained by a new synthetic route. The resolution of 4-amino-13-bromo[2.2]paracyclophane was achieved with relatively high efficiency. Starting from (4S p,13R p)-4-amino-13-bromo[2.2]paracyclophane, the planar chiral pseudogem-disubstituted [2.2]paracyclophanyl dihydroimidazoliums were prepared in a four-step sequence with good yields. The resulting dihydroimidazolium salts were fully characterized with a series of methods including single-crystal X-ray diffraction technique.</description><subject>Chemistry</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>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNptkE1rGzEQhkVpaZy0h_6BoksLOWwiaaX9OJZ10hQCMSTtpRQx1o7qTdcrd7Qb4n9fGRvnUl2ENA8v7zyMfZDiQgolLx9DJYQuqudXbCaNEllRC_2azYRQKstVkZ-w0xgfRTrGmLfsRFZaK1XLGfNzjN3vgcPQ8vvtMK7SM_Lg-aKHAYg3q46g5zc4IgW3dX3neAO0xAH5gtBNFANFPkfqnrDlnsKa_1QX6tcCCHZ82KxgwHfsjYc-4vvDfca-X189NDfZ7d3Xb82X2wy0LsdMidS8FVULsPSg29JpLbRZ6gJRyvSvfa5MXUDtULjc5UXry8rX6NLc1SY_Y5_3uRsKfyeMo1130WGflsEwRVvKQpmkIYHne9BRiJHQ2w11a6CtlcLupNqj1MR-PIROyzW2L-TBYgI-HQCIDnpPMLguHjkl8qqq5a5dtue6OOLzcQ70xxZlXhr7sLi3TVmJeVNc2x8vueBi6jPRkNz9p-A_lBaaZQ</recordid><startdate>20080606</startdate><enddate>20080606</enddate><creator>Duan, Wenzeng</creator><creator>Ma, Yudao</creator><creator>Xia, Houqi</creator><creator>Liu, Xueying</creator><creator>Ma, Qingshuang</creator><creator>Sun, Junshan</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20080606</creationdate><title>Design and Synthesis of Planar Chiral Heterocyclic Carbene Precursors Derived from [2.2]Paracyclophane</title><author>Duan, Wenzeng ; Ma, Yudao ; Xia, Houqi ; Liu, Xueying ; Ma, Qingshuang ; Sun, Junshan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a447t-20690d08daabfa4d7c44045b46ee1108d4f32596a9ce0c3c36df78f9ecee1c953</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Chemistry</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>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Duan, Wenzeng</creatorcontrib><creatorcontrib>Ma, Yudao</creatorcontrib><creatorcontrib>Xia, Houqi</creatorcontrib><creatorcontrib>Liu, Xueying</creatorcontrib><creatorcontrib>Ma, Qingshuang</creatorcontrib><creatorcontrib>Sun, Junshan</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</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>Duan, Wenzeng</au><au>Ma, Yudao</au><au>Xia, Houqi</au><au>Liu, Xueying</au><au>Ma, Qingshuang</au><au>Sun, Junshan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design and Synthesis of Planar Chiral Heterocyclic Carbene Precursors Derived from [2.2]Paracyclophane</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2008-06-06</date><risdate>2008</risdate><volume>73</volume><issue>11</issue><spage>4330</spage><epage>4333</epage><pages>4330-4333</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A unique family of planar chiral symmetrical N-heterocyclic carbene precursors with restricted flexibility derived from [2.2]paracyclopane were obtained by a new synthetic route. The resolution of 4-amino-13-bromo[2.2]paracyclophane was achieved with relatively high efficiency. Starting from (4S p,13R p)-4-amino-13-bromo[2.2]paracyclophane, the planar chiral pseudogem-disubstituted [2.2]paracyclophanyl dihydroimidazoliums were prepared in a four-step sequence with good yields. 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| source | American Chemical Society Journals |
| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Organic chemistry Preparations and properties |
| title | Design and Synthesis of Planar Chiral Heterocyclic Carbene Precursors Derived from [2.2]Paracyclophane |
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