The Activation of Imines to Nucleophilic Attack by Grignard Reagents
- 1 June 1988
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 18 (9) , 893-898
- https://doi.org/10.1080/00397918808060872
Abstract
The reaction of trimethylsilyl trifluoromethanesulfonate (trimethylsilyl triflate, TMSOTf) with imines leads to the formation of N-trimethylsilyliminium salts which react efficiently with soft nucleophiles to form secondary amines.Keywords
This publication has 6 references indexed in Scilit:
- Activated imines as carbon electrophiles: applications in alkaloid synthesisJournal of the Chemical Society, Chemical Communications, 1986
- Trimethylsilyl triflate-catalyzed 1,3-dipolar cycloaddition leading to N-unsubstituted pyrrolidines.CHEMICAL & PHARMACEUTICAL BULLETIN, 1985
- Reaction of silyl ketene acetals with N-trimethylsilyl imines: a route to N-unsubstituted azetidin-2-onesJournal of the Chemical Society, Chemical Communications, 1985
- N-Trimethylsilylimines: applications to the syntheses of .beta.-lactamsJournal of the American Chemical Society, 1984
- 1,3‐Anionische Cycloadditionen, XIV. Cycloaddition von 2‐Azaallyllithium‐Verbindungen an 1,3‐DieneEuropean Journal of Inorganic Chemistry, 1977
- A New Method for the Alkylation of Ketones and Aldehydes: the C-Alkylation of the Magnesium Salts of N-Substituted IminesJournal of the American Chemical Society, 1963