Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 13, Pages 2304-2315Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700313
Keywords
cyclization; in situ reduction; organocatalysis; phosphines; Wittig reaction
Categories
Funding
- French Agence Nationale de la Recherche (ANR) [ANR-13-JS07-0008]
- Centre National de la Recherche Scientifique (CNRS)
- Agence Nationale de la Recherche (ANR) [ANR-13-JS07-0008] Funding Source: Agence Nationale de la Recherche (ANR)
Ask authors/readers for more resources
The phosphine-catalyzed Michael addition/intramolecular Wittig reaction between dialkyl acetylenedicarboxylate and amino-carbaldehyde or amino ester derivatives has been developped. This reaction can be rendered catalytic in phosphine by the in situ chemoselective reduction of the phosphine oxide with silane. This methodology enables rapid access to a variety of nitrogen-containing heterocycles, which are present in numerous natural products and/or bioactive compounds. Either classical heating or microwave conditions give access to the desired products in good yields (15 examples, 60-99% yields). This catalytic methodology is further applicable to the synthesis of enantioenriched 1H-pyrrole derivatives, with the use of chiral phosphines. Finally, we successfully extended the reaction to the synthesis of a polysubstituted cyclopentenone, starting from butane-2,3-dione as substrate.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available