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One-pot three-component catalytic asymmetric 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 applied science and design. (Armando Córdova)ORCID iD: 0000-0002-5108-6487
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 applied science and design. (Armando Córdova)
2012 (English)In: ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY. Vol 243, American Chemical Society (ACS), 2012, 889-INOR- p.Conference paper, Oral presentation with published abstract (Refereed)
Abstract [en]

1. A novel one-pot three-component catalytic enantioselective reaction between bis(pinacolato)diboron, enals and 2-(triphenylphosphoranylidene)acetate esters employing inexpensive bench stable Cu salts and simple chiral amine as co-catalysts is presented. The reaction proceeds via a tandem catalytic asymmetric conjugate borane addition/Wittig sequence where the b-boration step is 1,4-selective and gives the corresponding homoallylboronate products with high enantiomeric ratios (up to 97.5:2.5 er).

2. The direct intermolecular regiospecific and highly enantioselective a-allylic alkylation of linear aldehydes by combination of achiral bench stable Pd(0) complexes and simple chiral amines as co-catalysts is disclosed. The co-catalytic asymmetric chemoselective and regiospecific a-allylic alkylation reaction is linked in tandem with in situ reduction to give the corresponding 2-alkyl alcohols with high enantiomeric ratios (up to 98:2 er). It is also an expeditious entry to valuable 2-alkyl substituted hemiacetals and 2-alkyl-butane-1,4-diols.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2012. 889-INOR- p.
Series
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, ISSN 0065-7727 ; 243
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:miun:diva-16701ISI: 000324503201250OAI: oai:DiVA.org:miun-16701DiVA: diva2:543941
Conference
Symposium on Ionic Liquids - Science and Applications / 243rd National Spring Meeting of the American-Chemical-Society
Available from: 2012-08-11 Created: 2012-08-11 Last updated: 2016-09-29Bibliographically approved

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Ibrahem, IsmailAfewerki, SamsonBreistein, PalleCórdova, Armando
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