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Enantioselective Palladium-Catalyzed Carbonylative Carbocyclization of Enallenes via Cross-Dehydrogenative Coupling with Terminal Alkynes: Efficient Construction of α-Chirality of Ketones.
Yang, Bin; Qiu, Youai; Jiang, Tuo; Wulff, William D; Yin, Xiaopeng; Zhu, Can; Bäckvall, Jan-E.
Affiliation
  • Yang B; Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm, Sweden.
  • Qiu Y; Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm, Sweden.
  • Jiang T; Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm, Sweden.
  • Wulff WD; Department of Chemistry, Michigan State University, MI, 48824, East Lansing, USA.
  • Yin X; Department of Chemistry, Michigan State University, MI, 48824, East Lansing, USA.
  • Zhu C; Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm, Sweden.
  • Bäckvall JE; Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm, Sweden.
Angew Chem Int Ed Engl ; 56(16): 4535-4539, 2017 04 10.
Article in En | MEDLINE | ID: mdl-28345175
An enantioselective PdII /Brønsted acid-catalyzed carbonylative carbocyclization of enallenes ending with a cross-dehydrogenative coupling (CDC) with a terminal alkyne was developed. VAPOL phosphoric acid was found as the best co-catalyst among the examined 28 chiral acids, for inducing the enantioselectivity of α-chiral ketones. As a result, a number of chiral cyclopentenones were easily synthesized in good to excellent enantiomeric ratio with good yields.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Angew Chem Int Ed Engl Year: 2017 Document type: Article Affiliation country: Suecia Country of publication: Alemania
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Angew Chem Int Ed Engl Year: 2017 Document type: Article Affiliation country: Suecia Country of publication: Alemania