Abstract
The tetrahedral intermediates generated upon the addition of halolithium carbenoids (LiCH2X and LiCHXY) to Weinreb amides have been intercepted and fully characterized as O-TMS heminals. The commercially available N-trimethylsilyl imidazole is the ideal trapping agent whose employment, combined with a straightforward neutral Alox chromatographic purification, enables the isolation of such labile species. The procedure could be advantageously extended also for obtaining O-TMS heminals from N-acylpyrroles. These intermediates manifest interesting reactivity including as precursors of more complex carbenoids.
Original language | English |
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Pages (from-to) | 9498-9501 |
Number of pages | 4 |
Journal | Chemical Communications |
Volume | 53 |
Issue number | 68 |
DOIs | |
Publication status | Published - 2017 |
Austrian Fields of Science 2012
- 104001 General chemistry
Keywords
- ALKYLATION
- CHEMOSELECTIVE KETONE SYNTHESIS
- DIRECT TRANSFORMATION
- EFFICIENT SYNTHESIS
- ORGANOLITHIUM REAGENTS
- ORGANOMETALLIC REAGENTS
- REACTIVITY CONTROL
- REDUCTIVE NUCLEOPHILIC-ADDITION
- SECONDARY AMIDES
- TRIFLIC ANHYDRIDE