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Asymmetric Synthesis of β-Substituted α-Methylenebutyro- lactones via TRIP-Catalyzed Allylation: Mechanistic Studies and Application to the Synthesis of (S)-(−)-Hydroxymatairesinol
Karl-FranzensUniversity Graz. (Faber)
Karl-FranzensUniversity Graz. (Faber)
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.ORCID iD: 0000-0001-5403-9902
Karl-Franzens University Graz. (Faber)
2013 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 355, no 13, 2499-2505 p.Article in journal (Refereed) Published
Abstract [en]

Asymmetric allylation of (hetero)aromatic aldehydes by a zinc(II)-allylbutyrolactone species catalyzed by a chiral BINOL-type phosphoric acid gave β-substituted α-methylenebutyrolactones in 68 to >99% ee and 52–91% isolated yield. DFT studies on the intermediate Zn2+-complex – crucial for chiral induction – suggest a six-membered ring intermediate, which allows the phosphoric acid moiety to activate the aldehyde. The methodology was applied to the synthesis of the antitumour natural product (S)-(−)-hydroxymatairesinol.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2013. Vol. 355, no 13, 2499-2505 p.
Keyword [en]
asymmetric allylation;butyrolactones;chiral phosphoric acids;hydroxymatairesinol;organozinc reagents
National Category
Natural Sciences Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
URN: urn:nbn:se:uu:diva-208323DOI: 10.1002/adsc.201300392ISI: 000327862400004OAI: diva2:651954
SNIC through Uppsala Multidisciplinary Center for Advanced Computational Science (UPPMAX). Grant Number: Project p2011197Austrian Science Fund (FWF). Grant Number: Erwin-Schrödinger-Fellowship (J3193-N17)
Available from: 2013-09-27 Created: 2013-09-27 Last updated: 2014-01-13Bibliographically approved

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