Enantioselective Intermolecular [2 + 2 + 2] Cycloadditions of Ene–Allenes with Allenoates
An enantioselective [2 + 2 + 2] cycloaddition of ene–allenes with allenoates is described, which transforms simple π-components into stereochemically complex carbocycles in a single step. The rhodium(I)-catalyzed cycloaddition proceeds with good levels of enantioselectivity, and with high levels of...
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| Published in | Organic letters Vol. 14; no. 23; pp. 6096 - 6099 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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WASHINGTON
American Chemical Society
07.12.2012
Amer Chemical Soc |
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| Abstract | An enantioselective [2 + 2 + 2] cycloaddition of ene–allenes with allenoates is described, which transforms simple π-components into stereochemically complex carbocycles in a single step. The rhodium(I)-catalyzed cycloaddition proceeds with good levels of enantioselectivity, and with high levels of regio-, chemo-, and diastereoselectivity. Our results are consistent with a mechanism involving an enantioselective intermolecular allene–allene oxidative coupling. |
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| AbstractList | An enantioselective [2 + 2 + 2] cycloaddition of ene-allenes with allenoates is described, which transforms simple pi-components into stereochemically complex carbocycles in a single step. The rhodium(I)-catalyzed cycloaddition proceeds with good levels of enantioselectivity, and with high levels of regio-, chemo-, and diastereoselectivity. Our results are consistent with a mechanism involving an enantioselective intermolecular allene-allene oxidative coupling. An enantioselective [2 + 2 + 2] cycloaddition of ene-allenes with allenoates is described, which transforms simple π-components into stereochemically complex carbocycles in a single step. The rhodium(I)-catalyzed cycloaddition proceeds with good levels of enantioselectivity, and with high levels of regio-, chemo-, and diastereoselectivity. Our results are consistent with a mechanism involving an enantioselective intermolecular allene-allene oxidative coupling. |
| Author | Brusoe, Andrew T Edwankar, Rahul V Alexanian, Erik J |
| AuthorAffiliation | The University of North Carolina at Chapel Hill |
| AuthorAffiliation_xml | – name: The University of North Carolina at Chapel Hill |
| Author_xml | – sequence: 1 givenname: Andrew T surname: Brusoe fullname: Brusoe, Andrew T – sequence: 2 givenname: Rahul V surname: Edwankar fullname: Edwankar, Rahul V – sequence: 3 givenname: Erik J surname: Alexanian fullname: Alexanian, Erik J email: eja@email.unc.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/23171471$$D View this record in MEDLINE/PubMed |
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| Keywords | ACETYLENES CYCLIZATIONS NICKEL LIGANDS NITRILES COMPLEXES ISOCYANATES ALKYNES DERIVATIVES DIYNES |
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| Snippet | An enantioselective [2 + 2 + 2] cycloaddition of ene–allenes with allenoates is described, which transforms simple π-components into stereochemically complex... An enantioselective [2 + 2 + 2] cycloaddition of ene-allenes with allenoates is described, which transforms simple pi-components into stereochemically complex... An enantioselective [2 + 2 + 2] cycloaddition of ene-allenes with allenoates is described, which transforms simple π-components into stereochemically complex... |
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| Title | Enantioselective Intermolecular [2 + 2 + 2] Cycloadditions of Ene–Allenes with Allenoates |
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