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Synlett 2004(6): 1092-1094
DOI: 10.1055/s-2004-822896
DOI: 10.1055/s-2004-822896
LETTER
© Georg Thieme Verlag Stuttgart · New York
A Simple One-pot Organometallic Formylation/Trapping Sequence Using N-Formylcarbazole
Weitere Informationen
Received
30 January 2004
Publikationsdatum:
25. März 2004 (online)
Publikationsverlauf
Publikationsdatum:
25. März 2004 (online)
Abstract
Treatment of a range of sp3-, sp2- and sp-nucleophiles with N-formyl carbazole leads to the formation of the metastable anionic carbazole carbinols. In the presence of a second nucleophilic reagent such as phosphonoacetate or an organolithium, these collapse on warming to the aldehyde which is trapped in situ to afford the α,β-unsaturated esters or secondary carbinols respectively.
Key words
carbinols - enynes - formylation - heterocycles - N-formylcarbazole
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