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[]Dendralenes as a Platform for Selective Catalysis: Ligand-Controlled Cu-Catalyzed Chemo-, Regio-, and Enantioselective Borylations.
Org Lett
November 2020
Department of Organic Chemistry, University of Geneva, 30 quai Ernest Ansermet, 1211 Geneva, Switzerland.
We report the development of two complementary methods for the Cu-catalyzed -Markovnikov borylation of one specific olefin in 2-substituted []dendralenes ( = 3-6). The first protocol operates with a bisphosphine ligand and occurs with high regio- and chemoselectivity for the terminal double bond, independently of the number of cross-conjugated alkenes. We show that the use of a chiral phosphanamine ligand enables the highly chemo-, regio-, and enantioselective borylation of the alkene cross-conjugated with the terminal olefin in []dendralenes.
View Article and Find Full Text PDFSynthesis and Properties of 2,3-Diethynyl-1,3-Butadienes.
Angew Chem Int Ed Engl
March 2020
Research School of Chemistry, Australian National University, Canberra, ACT, 2601, Australia.
The first general preparative access to compounds of the 2,3-diethynyl-1,3-butadiene (DEBD) class is reported. The synthesis involves a one-pot, twofold Sonogashira-type, Pd -catalyzed coupling of two terminal alkynes and a carbonate derivative of a 2-butyne-1,4-diol. The synthesis is broad in scope and members of this structural family are kinetically stable enough to be handled using standard laboratory techniques at ambient temperature.
View Article and Find Full Text PDFDiene-Transmissive Enantioselective Diels-Alder Reactions and Sequences Involving Substituted Dendralenes.
J Org Chem
November 2019
Research School of Chemistry , The Australian National University, Canberra , ACT 2601 , Australia.
Readily available and stable substituted [3]dendralenes undergo highly chemo-, regio-, diastereo-, and enantioselective organocatalyzed Diels-Alder reactions with acrolein to form enantiomerically enriched cycloadducts. These monocycloadducts carry semicyclic dienes that undergo a second, substrate-controlled diastereoselective Diels-Alder reaction with a different dienophile to form 2-fold cycloadducts. Overall, annulated, functional group rich, chiral Δ-octalin building blocks are accessed in one-pot operations that significantly extend the preparative value of diene-transmissive Diels-Alder sequences since they offer products of regio- and stereochemistry complementary to those generated from the parent, unsubstituted [3]dendralene.
View Article and Find Full Text PDFControl of Selectivity in Palladium(II)-Catalyzed Oxidative Transformations of Allenes.
Acc Chem Res
June 2018
Department of Organic Chemistry, Arrhenius Laboratory , Stockholm University, SE-106 91 Stockholm , Sweden.
Oxidation reactions play a central role in organic synthesis, and it is highly desirable that these reactions are mild and occur under catalytic conditions. In Nature, oxidation reactions occur under mild conditions via cascade processes, and furthermore, they often occur in an enantioselective manner with many of them involving molecular oxygen or hydrogen peroxide as the terminal oxidant. Inspired by the reactions in Nature, we have developed a number of Pd(II)-catalyzed cascade reactions under mild oxidative conditions.
View Article and Find Full Text PDFChiral dendralenes for rapid access to enantiomerically pure polycycles.
Angew Chem Int Ed Engl
May 2007
Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia.
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