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Regioselective Preparation of Functionalized exo-Methylene-cyclopentanes and exo-Methylenepyrrolidines via Silaborative Carbocyclization of 1,6-Enynes
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.ORCID iD: 0000-0002-1743-7650
2010 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 352, no 14-15, 2559-2570 p.Article in journal (Refereed) Published
Abstract [en]

Silaborative carbocyclization of 1,6-enynes catalyzed by Pd-PEPPSI-IPr {PEPPSI=pyridine-enhanced precatalyst preparation stabilization and initiation; IPr=N,N-bis[2,6-(diisopropyl)phenyl] imidazolium} employing either (dimethylphenylsilyl) pinacolborane or (chlorodimethylsilyl)pinacolborane provides access to densely functionalized five-membered rings as single diastereomers in excellent yields. The vinylboronate functions were employed in palladium-catalyzed Suzuki cross-coupling reactions with a range of aryl bromides, containing electron-with-drawing as well as electron-donating substituents, furnishing arylated exo-methylenecyclopentanes or exo-methylenepyrrolidines in good yields. Subsequent oxidation of the isopropoxydimethylsilyl function generated via addition of (chlorodimethylsilyl)-pinacolborane provided access to hydroxymethyl derivatives of the arylated compounds. Use of a chiral ester, bismenthyl (2-propenyl)(2-propynyl)malonate, afforded two diastereomeric products which could be separated, thereby giving access to the cyclized compounds as single isomers, with opposite absolute configurations at the newly formed stereocenter.

Place, publisher, year, edition, pages
2010. Vol. 352, no 14-15, 2559-2570 p.
Keyword [en]
cross-coupling, cyclization, enynes, oxidation, palladium, silylboranes
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-27105DOI: 10.1002/adsc.201000434ISI: 000284003100032Scopus ID: 2-s2.0-78349270814OAI: oai:DiVA.org:kth-27105DiVA: diva2:375769
Note
QC 20101209Available from: 2010-12-09 Created: 2010-12-06 Last updated: 2017-12-11Bibliographically approved

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Moberg, Christina

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