The Au(I) Catalyzed Activation of Allenamides and Their Subsequent Transformation into Chromanes: A Method for the Regiocontrolled Addition to the α- and γ-Positions of the Allene Unit

Slater, Natasha H.; Brown, Natalie J.; Elsegood, Mark R. J.; Kimber, Marc C.

Abstract

Au(I) activation of allenamides in the presence of phenols leads to the formation of chromanes in moderate to good yields. This catalytic process is dependent on the counterion which facilitates the activation of the in situ formed imine. Furthermore, this iminium can be intercepted by trimethylallyl silane, via the Hosomi–Sakurai reaction, giving a formal procedure for the regioselective intermolecular addition of two carbon nucleophiles to an allenamide at the α- and γ-positions.

• Journal Article Type: Article
• Online Publication Date: Aug 14, 2014
• Publication Date: Sep 5, 2014
• Deposit Date: Jun 16, 2023
• Journal: Organic Letters
• Print ISSN: 1523-7060
• Electronic ISSN: 1523-7052
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 16
• Issue: 17
• Pages: 4606-4609
• DOI: https://doi.org/10.1021/ol502178v
• Keywords: Organic Chemistry; Physical and Theoretical Chemistry; Biochemistry