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Asymmetric Synthesis of Overcrowded Alkenes by Transfer of Axial Single Bond Chirality to Axial Double Bond Chirality

1999; Wiley; Volume: 38; Issue: 18 Linguagem: Inglês

10.1002/(sici)1521-3773(19990917)38

1521-3773

Edzard M. Geertsema, Auke Meetsma, Ben L. Feringa,

Synthesis and Properties of Aromatic Compounds

Angewandte Chemie International EditionVolume 38, Issue 18 p. 2738-2741 Communication Asymmetric Synthesis of Overcrowded Alkenes by Transfer of Axial Single Bond Chirality to Axial Double Bond Chirality Edzard M. Geertsema, Edzard M. Geertsema Department of Organic and Molecular Inorganic Chemistry, University of Groningen, Nijenborgh 4, NL-9747 AG Groningen (The Netherlands), Fax: (+31) 50-363-4296Search for more papers by this authorAuke Meetsma, Auke Meetsma Department of Organic and Molecular Inorganic Chemistry, University of Groningen, Nijenborgh 4, NL-9747 AG Groningen (The Netherlands), Fax: (+31) 50-363-4296Search for more papers by this authorBen L. Feringa, Ben L. Feringa feringa@chem.rug.nl Department of Organic and Molecular Inorganic Chemistry, University of Groningen, Nijenborgh 4, NL-9747 AG Groningen (The Netherlands), Fax: (+31) 50-363-4296Search for more papers by this author Edzard M. Geertsema, Edzard M. Geertsema Department of Organic and Molecular Inorganic Chemistry, University of Groningen, Nijenborgh 4, NL-9747 AG Groningen (The Netherlands), Fax: (+31) 50-363-4296Search for more papers by this authorAuke Meetsma, Auke Meetsma Department of Organic and Molecular Inorganic Chemistry, University of Groningen, Nijenborgh 4, NL-9747 AG Groningen (The Netherlands), Fax: (+31) 50-363-4296Search for more papers by this authorBen L. Feringa, Ben L. Feringa feringa@chem.rug.nl Department of Organic and Molecular Inorganic Chemistry, University of Groningen, Nijenborgh 4, NL-9747 AG Groningen (The Netherlands), Fax: (+31) 50-363-4296Search for more papers by this author First published: 15 September 1999 https://doi.org/10.1002/(SICI)1521-3773(19990917)38:18 3.0.CO;2-ZCitations: 16AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Abstract Optically active overcrowded alkenes were synthesized by employing bis-β-naphthol as a chiral template during an intramolecular coupling reaction. The major isomer 2 has a unique helical structure with twisted and folded structural moieties. Removal of the chiral template afforded overcrowded thioxanthylidene 3 with 96 % ee, which indicates that no racemization or isomerization of the enantiomers took place. Citing Literature Volume38, Issue18September 17, 1999Pages 2738-2741 RelatedInformation