Research Article: Asymmetric Synthesis of β-Substituted α-Methylenebutyro- lactones via TRIP-Catalyzed Allylation: Mechanistic Studies and Application to the Synthesis of (S)-(−)-Hydroxymatairesinol

Date Published: September 16, 2013

Publisher: WILEY-VCH Verlag

Author(s): Michael Fuchs, Markus Schober, Andreas Orthaber, Kurt Faber.

http://doi.org/10.1002/adsc.201300392

Abstract

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.

Partial Text

 

Source:

http://doi.org/10.1002/adsc.201300392

 

Leave a Reply

Your email address will not be published.