Unprecedented Regio- and Stereoselective Conversion of 1-Cyclopropyl-3-ethoxycyclopentadienes to 3-(E)-Alkylidenecyclopentenes

Cyclopropylalkynes 1 were converted into cyclopropyl-substituted 3-ethoxy-5-dimethylaminocyclopentadienes 4 via initially formed (β-dimethylaminoethenyl)carbene complexes 3 and their subsequent formal [3 + 2] cycloaddition to a second alkyne of type 1 (overall yields 51−59%). New regio- and stereose...

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Published in:Journal of organic chemistry 1999-01, Vol.64 (2), p.400-404
Main Authors: Flynn, Bernard L, de Meijere, Armin
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Language:English
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description Cyclopropylalkynes 1 were converted into cyclopropyl-substituted 3-ethoxy-5-dimethylaminocyclopentadienes 4 via initially formed (β-dimethylaminoethenyl)carbene complexes 3 and their subsequent formal [3 + 2] cycloaddition to a second alkyne of type 1 (overall yields 51−59%). New regio- and stereoselective 1,7-addition and 1,6-substitution reactions have been developed that convert cyclopentadienes 4 into highly functionalized cyclopentenes 5 and 11, respectively (yields 98−99% and 61%, respectively). An in situ domino reaction consisting of a [3 + 2] cycloaddition and subsequent 1,7-addition has also been achieved (86% overall yield).
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Org. Chem</addtitle><date>1999-01-22</date><risdate>1999</risdate><volume>64</volume><issue>2</issue><spage>400</spage><epage>404</epage><pages>400-404</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Cyclopropylalkynes 1 were converted into cyclopropyl-substituted 3-ethoxy-5-dimethylaminocyclopentadienes 4 via initially formed (β-dimethylaminoethenyl)carbene complexes 3 and their subsequent formal [3 + 2] cycloaddition to a second alkyne of type 1 (overall yields 51−59%). New regio- and stereoselective 1,7-addition and 1,6-substitution reactions have been developed that convert cyclopentadienes 4 into highly functionalized cyclopentenes 5 and 11, respectively (yields 98−99% and 61%, respectively). An in situ domino reaction consisting of a [3 + 2] cycloaddition and subsequent 1,7-addition has also been achieved (86% overall yield).</abstract><pub>American Chemical Society</pub><doi>10.1021/jo980938z</doi><tpages>5</tpages></addata></record>
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title Unprecedented Regio- and Stereoselective Conversion of 1-Cyclopropyl-3-ethoxycyclopentadienes to 3-(E)-Alkylidenecyclopentenes
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