Regio- and diastereoselective dearomatizations of N -alkyl activated azaarenes: the maximization of the reactive sites
An unprecedented base-promoted multi-component one-pot dearomatization of N -alkyl activated azaarenes was developed, which enabled the synthesis of complex and diverse bridged cyclic polycycles with multiple stereocenters in a highly regio- and diastereoselective manner. Besides, we realized the st...
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Veröffentlicht in: | Chemical science (Cambridge) 2020, Vol.11 (5), p.1418-1424 |
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creator | Miao, Hong-Jie Wang, Le-Le Han, Hua-Bin Zhao, Yong-De Wang, Qi-Lin Bu, Zhan-Wei |
description | An unprecedented base-promoted multi-component one-pot dearomatization of
N
-alkyl activated azaarenes was developed, which enabled the synthesis of complex and diverse bridged cyclic polycycles with multiple stereocenters in a highly regio- and diastereoselective manner. Besides, we realized the step-controlled dearomative bi- and trifunctionalization of quinolinium salts. These transformations not only achieved the maximization of the reaction sites of pyridinium, quinolinium and isoquinolinium salts to enhance structural complexity and diversity, but also opened up a new reaction mode of these
N
-activated azaarenes. A unique feature of this strategy is the use of easily accessible and bench-stable
N
-alkyl activated azaarenes to provide maximum reactive sites for dearomative cascade cyclizations. In addition, the salient characteristics including high synthetic efficiency, short reaction time, mild conditions and simple operation made this strategy particularly attractive. |
doi_str_mv | 10.1039/c9sc04880d |
format | Article |
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N
-alkyl activated azaarenes was developed, which enabled the synthesis of complex and diverse bridged cyclic polycycles with multiple stereocenters in a highly regio- and diastereoselective manner. Besides, we realized the step-controlled dearomative bi- and trifunctionalization of quinolinium salts. These transformations not only achieved the maximization of the reaction sites of pyridinium, quinolinium and isoquinolinium salts to enhance structural complexity and diversity, but also opened up a new reaction mode of these
N
-activated azaarenes. A unique feature of this strategy is the use of easily accessible and bench-stable
N
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N
-alkyl activated azaarenes was developed, which enabled the synthesis of complex and diverse bridged cyclic polycycles with multiple stereocenters in a highly regio- and diastereoselective manner. Besides, we realized the step-controlled dearomative bi- and trifunctionalization of quinolinium salts. These transformations not only achieved the maximization of the reaction sites of pyridinium, quinolinium and isoquinolinium salts to enhance structural complexity and diversity, but also opened up a new reaction mode of these
N
-activated azaarenes. A unique feature of this strategy is the use of easily accessible and bench-stable
N
-alkyl activated azaarenes to provide maximum reactive sites for dearomative cascade cyclizations. In addition, the salient characteristics including high synthetic efficiency, short reaction time, mild conditions and simple operation made this strategy particularly attractive.</description><subject>Chemistry</subject><subject>Complexity</subject><subject>Crystallography</subject><subject>Maximization</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Optimization</subject><subject>Reaction time</subject><subject>Stereoselectivity</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpdkVtrFTEQx4MotrR98RMEfBFhNbfNxQdBjtoKpQUvz2HMzrapu5ua5BxsP705nkOhDgwzZH7zZzJDyAvO3nAm3dvgSmDKWjY8IYeCKd7pXrqnD7lgB-SklBvWTEreC_OcHEjFhRRaH5LNV7yKqaOwDHSIUCpmTAUnDDVukA4IOc1Q433ztBSaRnpBO5h-3U0UtgxUHCjcA2RcsLyj9RrpDH_ivG_ZdmzfMsJOssSK5Zg8G2EqeLKPR-TH50_fV2fd-eXpl9WH8y5IZWonmBZu1KDQGM6MdlY57kQflDXWKAja9hbBjnpgViil-2FUDbetAgy4PCLvd7q3658zDgGXmmHytznOkO98gugfV5Z47a_SxluujHWqCbzaC-T0e42l-jmWgNMEC6Z18aJXzIi2TNbQl_-hN2mdl_Y9L2TPHBNW20a93lEhp1Iyjg_DcOa3F_Ur923176If5V_aPJKi</recordid><startdate>2020</startdate><enddate>2020</enddate><creator>Miao, Hong-Jie</creator><creator>Wang, Le-Le</creator><creator>Han, Hua-Bin</creator><creator>Zhao, Yong-De</creator><creator>Wang, Qi-Lin</creator><creator>Bu, Zhan-Wei</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-4637-0392</orcidid></search><sort><creationdate>2020</creationdate><title>Regio- and diastereoselective dearomatizations of N -alkyl activated azaarenes: the maximization of the reactive sites</title><author>Miao, Hong-Jie ; Wang, Le-Le ; Han, Hua-Bin ; Zhao, Yong-De ; Wang, Qi-Lin ; Bu, Zhan-Wei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c347t-20629f6a4e77107698491925c487874ac6858ea8f6d0824465df46a48ac6a0a13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Chemistry</topic><topic>Complexity</topic><topic>Crystallography</topic><topic>Maximization</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Optimization</topic><topic>Reaction time</topic><topic>Stereoselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Miao, Hong-Jie</creatorcontrib><creatorcontrib>Wang, Le-Le</creatorcontrib><creatorcontrib>Han, Hua-Bin</creatorcontrib><creatorcontrib>Zhao, Yong-De</creatorcontrib><creatorcontrib>Wang, Qi-Lin</creatorcontrib><creatorcontrib>Bu, Zhan-Wei</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Miao, Hong-Jie</au><au>Wang, Le-Le</au><au>Han, Hua-Bin</au><au>Zhao, Yong-De</au><au>Wang, Qi-Lin</au><au>Bu, Zhan-Wei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regio- and diastereoselective dearomatizations of N -alkyl activated azaarenes: the maximization of the reactive sites</atitle><jtitle>Chemical science (Cambridge)</jtitle><date>2020</date><risdate>2020</risdate><volume>11</volume><issue>5</issue><spage>1418</spage><epage>1424</epage><pages>1418-1424</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>An unprecedented base-promoted multi-component one-pot dearomatization of
N
-alkyl activated azaarenes was developed, which enabled the synthesis of complex and diverse bridged cyclic polycycles with multiple stereocenters in a highly regio- and diastereoselective manner. Besides, we realized the step-controlled dearomative bi- and trifunctionalization of quinolinium salts. These transformations not only achieved the maximization of the reaction sites of pyridinium, quinolinium and isoquinolinium salts to enhance structural complexity and diversity, but also opened up a new reaction mode of these
N
-activated azaarenes. A unique feature of this strategy is the use of easily accessible and bench-stable
N
-alkyl activated azaarenes to provide maximum reactive sites for dearomative cascade cyclizations. In addition, the salient characteristics including high synthetic efficiency, short reaction time, mild conditions and simple operation made this strategy particularly attractive.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><pmid>34123266</pmid><doi>10.1039/c9sc04880d</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0003-4637-0392</orcidid><oa>free_for_read</oa></addata></record> |
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subjects | Chemistry Complexity Crystallography Maximization NMR Nuclear magnetic resonance Optimization Reaction time Stereoselectivity |
title | Regio- and diastereoselective dearomatizations of N -alkyl activated azaarenes: the maximization of the reactive sites |
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