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One-Pot Three-Component Catalytic Enantioselective Synthesis of Homoallylboronates
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics. (Armando Córdova)
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics. (Armando Córdova)
2011 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, no 50, 12036-12041 p.Article in journal (Refereed) Published
Abstract [en]

No longer a simple bor(ation): The title reaction between bis(pinacolato)diboron, enals, and 2-(triphenylphosphoranylidene)acetates employing bench-stable copper salts and a simple chiral amine co-catalyst is presented. The reaction proceeds through a catalytic asymmetric conjugate borane addition/Wittig sequence wherein the β-boration step is 1,4-selective and gives the corresponding homoallylboronate products with high enantiomeric ratios.

Place, publisher, year, edition, pages
2011. Vol. 50, no 50, 12036-12041 p.
Keyword [en]
asymmetric catalysis; boron; conjugate additions; multicomponent reactions; Wittig reactions
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:miun:diva-14747DOI: 10.1002/anie.201105458ISI: 000298085000036PubMedID: 22006571Scopus ID: 2-s2.0-83455198235OAI: oai:DiVA.org:miun-14747DiVA: diva2:457145
Available from: 2011-11-16 Created: 2011-11-16 Last updated: 2012-05-16Bibliographically approved
In thesis
1. Development of highly enantioselective organocatalyzed transformations
Open this publication in new window or tab >>Development of highly enantioselective organocatalyzed transformations
2011 (English)Doctoral thesis, comprehensive summary (Other academic)
Place, publisher, year, edition, pages
Sundsvall: Mid Sweden University, 2011. 48 p.
Series
Mid Sweden University doctoral thesis, ISSN 1652-893X ; 117
Keyword
Asymetric catalysis, aldehydes, proline derivatives, transition metals, Friedel-Crafts, conjugate addition, boration, α-alkylation
National Category
Organic Chemistry
Identifiers
urn:nbn:se:miun:diva-15621 (URN)978-91-86694-61-6 (ISBN)
Supervisors
Available from: 2011-12-22 Created: 2011-12-22 Last updated: 2012-07-30Bibliographically approved

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