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Stereoselective Synthesis of Trisubstituted E-Iodoalkenes by Indium-Catalyzed syn-Addition of 1,3-Dicarbonyl Compounds to 1-Iodoalkynes
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Abstract
Indium-catalyzed addition of 1,3-dicarbonyl compounds to 1-iodo-1-alkynes takes place exclusively in a syn-fashion to produce E-iodoalkenes. The iodine atom serves both as an activating group and as a group that controls the regioselectivity of the addition. The E-alkenyl iodide product can be further derivatized using either a one-pot or a two-pot procedure into trisubstituted olefins in high overall yield with retention of the stereochemistry.
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This article has been cited by 7 ACS Journal articles (5 most recent appear below).
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Indium-Catalyzed [1 + n] Annulation Reaction between β-Ketoester and α,ω-Diyne
Hayato Tsuji, Iku Tanaka, Kohei Endo, Ken-ichi Yamagata, Masaharu Nakamura and Eiichi NakamuraOrganic Letters2009 11 (8), 1845-1847Indium-Catalyzed [1 + n] Annulation Reaction between β-Ketoester and α,ω-Diyne
Hayato Tsuji, Iku Tanaka, Kohei Endo, Ken-ichi Yamagata, Masaharu Nakamura and Eiichi NakamuraOrganic Letters2009 11 (8), 1845-1847A catalytic amount of In(NTf2)3 effects the inter- and intramolecular addition of a β-ketoester to an α,ω-diyne to produce a 1,3-dimethylenecycloalkane derivative in a single step. This [1 + n] annulation reaction shows good functional group tolerance ...
Mechanistic Study of the Manganese-Catalyzed [2 + 2 + 2] Annulation of 1,3-Dicarbonyl Compounds and Terminal Alkynes
Naohiko Yoshikai, Song-Lin Zhang, Ken-ichi Yamagata, Hayato Tsuji and Eiichi NakamuraJournal of the American Chemical Society2009 131 (11), 4099-4109Mechanistic Study of the Manganese-Catalyzed [2 + 2 + 2] Annulation of 1,3-Dicarbonyl Compounds and Terminal Alkynes
Naohiko Yoshikai, Song-Lin Zhang, Ken-ichi Yamagata, Hayato Tsuji and Eiichi NakamuraJournal of the American Chemical Society2009 131 (11), 4099-4109The manganese-catalyzed dehydrative [2 + 2 + 2] annulation reaction of a 1,3-dicarbonyl compound and a terminal alkyne provides an efficient and regioselective synthesis of a substituted benzene derivative, highlighted by the exclusive formation of a p-...
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History
- Published In Issue March 20, 2008
- Received January 16, 2008
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