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Rh-Catalyzed Intermolecular Cyclopropanation with α-Alkyl-α-diazoesters: Catalyst-Dependent Chemo- and Diastereoselectivity
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Abstract
A Rh-catalyzed procedure for the cyclopropanation of alkenes with α-alkyl-α-diazoesters is described. With dirhodium tetraoctanoate, the predominant pathway is β-hydride elimination. While a number of sterically demanding carboxylate ligands serve to avoid β-hydride elimination, it was found that triphenylacetate (TPA) also imparts high diastereoselectivity.
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This article has been cited by 7 ACS Journal articles (5 most recent appear below).
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Rhodium(II)-Catalyzed Enantioselective C−H Functionalization of Indoles
Andrew DeAngelis, Valerie W. Shurtleff, Olga Dmitrenko, and Joseph M. FoxJournal of the American Chemical Society2011 133 (6), 1650-1653Rhodium(II)-Catalyzed Enantioselective C−H Functionalization of Indoles
Andrew DeAngelis, Valerie W. Shurtleff, Olga Dmitrenko, and Joseph M. FoxJournal of the American Chemical Society2011 133 (6), 1650-1653A catalytic, enantioselective method for the C−H functionalization of indoles by diazo compounds has been achieved. With catalytic amounts of Rh2(S-NTTL)4, the putative Rh−carbene intermediates from α-alkyl-α-diazoesters react with indoles at C(3) to ...
Synthesis and Reactivity of Rhodium(II) N-Triflyl Azavinyl Carbenes
Neil Grimster, Li Zhang and Valery V. FokinJournal of the American Chemical Society2010 132 (8), 2510-2511Synthesis and Reactivity of Rhodium(II) N-Triflyl Azavinyl Carbenes
Neil Grimster, Li Zhang and Valery V. FokinJournal of the American Chemical Society2010 132 (8), 2510-2511Highly reactive rhodium(II) N-trifluoromethylsulfonyl azavinyl carbenes are formed in situ from NH-1,2,3-triazoles, triflic anhydride, and rhodium carboxylates. They rapidly and selectively react with olefins, providing cyclopropane carboxaldehydes and 2,...
Chiral Crown Conformation of Rh2(S-PTTL)4: Enantioselective Cyclopropanation with α-Alkyl-α-diazoesters
Andrew DeAngelis, Olga Dmitrenko, Glenn P. A. Yap and Joseph M. FoxJournal of the American Chemical Society2009 131 (21), 7230-7231Chiral Crown Conformation of Rh2(S-PTTL)4: Enantioselective Cyclopropanation with α-Alkyl-α-diazoesters
Andrew DeAngelis, Olga Dmitrenko, Glenn P. A. Yap and Joseph M. FoxJournal of the American Chemical Society2009 131 (21), 7230-7231Herein, we provide crystallographic and computational evidence that Hashimoto’s Rh2(S-PTTL)4 catalyst adopts a “chiral crown” conformation with a reactive chiral face and an unreactive achiral face. In Rh2(S-PTTL)4, all four tert-butyl groups are aligned ...
Directed Carbozincation Reactions of Cyclopropene Derivatives
Vinod Tarwade, Xiaozhong Liu, Ni Yan and Joseph M. FoxJournal of the American Chemical Society2009 131 (15), 5382-5383Directed Carbozincation Reactions of Cyclopropene Derivatives
Vinod Tarwade, Xiaozhong Liu, Ni Yan and Joseph M. FoxJournal of the American Chemical Society2009 131 (15), 5382-5383A diastereoselective procedure has been developed for the Cu-catalyzed addition of diorganozinc reagents to cyclopropene derivatives. Ester and oxazolidinone functions direct the addition of a variety of organozinc reagents with excellent facial ...
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History
- Published In Issue July 17, 2008
- Article ASAPJune 12, 2008
- Received: April 29, 2008
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