Synlett 2004(6): 1092-1094  
DOI: 10.1055/s-2004-822896
LETTER
© Georg Thieme Verlag Stuttgart · New York

A Simple One-pot Organometallic Formylation/Trapping Sequence Using N-Formylcarbazole

Darren J. Dixon*, Amanda C. LucasUniversity Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK
Fax: +44(1223)336362; e-Mail: djd26@cam.ac.uk;
Further Information

Publication History

Received 30 January 2004
Publication Date:
25 March 2004 (eFirst)

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.