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Development of highly enantioselective organocatalyzed transformations
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
2011 (English)Doctoral thesis, comprehensive summary (Other academic)
Place, publisher, year, edition, pages
Sundsvall: Mid Sweden University , 2011. , p. 48
Series
Mid Sweden University doctoral thesis, ISSN 1652-893X ; 117
Keywords [en]
Asymetric catalysis, aldehydes, proline derivatives, transition metals, Friedel-Crafts, conjugate addition, boration, α-alkylation
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:miun:diva-15621ISBN: 978-91-86694-61-6 (print)OAI: oai:DiVA.org:miun-15621DiVA, id: diva2:469069
Supervisors
Available from: 2011-12-22 Created: 2011-12-22 Last updated: 2012-07-30Bibliographically approved
List of papers
1. Chiral pyrrolidinium salts as organocatalysts in stereoselective 1,4-conjugate addition of N-methylpyrrole to cyclopent-1-ene carbaldehyde
Open this publication in new window or tab >>Chiral pyrrolidinium salts as organocatalysts in stereoselective 1,4-conjugate addition of N-methylpyrrole to cyclopent-1-ene carbaldehyde
2006 (English)In: Tetrahedron: Asymmetry, ISSN 0957-4166, Vol. 17, no 1, p. 107-111Article in journal (Refereed) Published
Keywords
organo-catalysts, stereoselectivity, synthesis
National Category
Chemical Sciences
Identifiers
urn:nbn:se:miun:diva-3265 (URN)10.1016/j.tetasy.2005.11.020 (DOI)000235271200015 ()2-s2.0-30944445374 (Scopus ID)4000 (Local ID)4000 (Archive number)4000 (OAI)
Available from: 2008-09-30 Created: 2008-09-30 Last updated: 2016-09-29Bibliographically approved
2. One-step catalytic enantioselective 5-hydroxy-α-quaternary proline synthesis: An asymmetric entry to highly functionalized α-quaternary proline derivatives
Open this publication in new window or tab >>One-step catalytic enantioselective 5-hydroxy-α-quaternary proline synthesis: An asymmetric entry to highly functionalized α-quaternary proline derivatives
Show others...
(English)Manuscript (preprint) (Other academic)
National Category
Organic Chemistry
Identifiers
urn:nbn:se:miun:diva-14749 (URN)
Available from: 2011-11-16 Created: 2011-11-16 Last updated: 2013-09-05Bibliographically approved
3. Catalytic Enantioselective beta-Alkylation of alpha,beta-Unsaturated Aldehydes by Combination of Transition-Metal- and Aminocatalysis: Total Synthesis of Bisabolane Sesquiterpenes
Open this publication in new window or tab >>Catalytic Enantioselective beta-Alkylation of alpha,beta-Unsaturated Aldehydes by Combination of Transition-Metal- and Aminocatalysis: Total Synthesis of Bisabolane Sesquiterpenes
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2011 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 17, no 32, p. 8784-8788Article in journal (Refereed) Published
Abstract [en]

Branching out! The first co-catalytic enantioselective (up to 98:2 e.r.) β-alkylation of α,β-unsaturated aldehydes by combination of simple chiral amine and copper catalysts provides β-branched aldehydes in a one-pot protocol (see scheme). The methodology was applied to the short total syntheses of bisabolane sesquiterpenes (S)-(+)-curcumene, (E)-(S)-(+)-3- dehydrocurcumene and (S)-(+)-tumerone. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords
aldehydes; alkylation; asymmetric conjugate additions; enantioselectivity; co-catalysis; zinc
National Category
Organic Chemistry
Identifiers
urn:nbn:se:miun:diva-14528 (URN)10.1002/chem.201100756 (DOI)000294704700003 ()2-s2.0-79960754105 (Scopus ID)
Available from: 2011-09-23 Created: 2011-09-23 Last updated: 2017-12-08Bibliographically approved
4. One-Pot Three-Component Catalytic Enantioselective Synthesis of Homoallylboronates
Open this publication in new window or tab >>One-Pot Three-Component Catalytic Enantioselective Synthesis of Homoallylboronates
2011 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, no 50, p. 12036-12041Article 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.

Keywords
asymmetric catalysis; boron; conjugate additions; multicomponent reactions; Wittig reactions
National Category
Organic Chemistry
Identifiers
urn:nbn:se:miun:diva-14747 (URN)10.1002/anie.201105458 (DOI)000298085000036 ()22006571 (PubMedID)2-s2.0-83455198235 (Scopus ID)
Available from: 2011-11-16 Created: 2011-11-16 Last updated: 2017-12-08Bibliographically approved
5. Direct Regiospecific and Highly Enantioselective Intermolecular α-Allylic Alkylation of Aldehydes By Combination of Transition Metal and amine Catalysts
Open this publication in new window or tab >>Direct Regiospecific and Highly Enantioselective Intermolecular α-Allylic Alkylation of Aldehydes By Combination of Transition Metal and amine Catalysts
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2012 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 10, p. 2972-2977Article in journal (Refereed) Published
Abstract [en]

The first direct intermolecular regiospecific and highly enantioselective α-allylic alkylation of linear aldehydes by a combination of achiral bench-stable Pd 0 complexes and simple chiral amines as co-catalysts is disclosed. The co-catalytic asymmetric chemoselective and regiospecificα-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 e.r.; e.r.=enantiomeric ratio). It is also an expeditious entry to valuable 2-alkyl substituted hemiacetals, 2-alkyl-butane-1,4-diols, and amines. The concise co-catalytic asymmetric total syntheses of biologically active natural products (e.g., Arundic acid) are disclosed. Go organic! Directintermolecular regiospecific and highly enantioselective α-allylic alkylation of linear aldehydes by a combination of achiral bench-stable Pd 0complexes and simple chiral amines as co-catalysts is disclosed (see scheme). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords
aldehydes; allylation; asymmetric catalysis; co-catalysis; transition metals
National Category
Organic Chemistry
Identifiers
urn:nbn:se:miun:diva-14579 (URN)10.1002/chem.201103366 (DOI)000300837100028 ()2-s2.0-84857544234 (Scopus ID)
Available from: 2011-10-05 Created: 2011-10-05 Last updated: 2017-12-08Bibliographically approved

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Palle Breistein doctoral thesis(1203 kB)727 downloads
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Breistein, Palle

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