Lewis Acid Catalyzed Room-Temperature Michaelis-Arbuzov Rearrangement

The taming of the shrew! For the first time, a broadly applicable efficient room‐temperature Arbuzov rearrangement is described. This reaction is accomplished through an atom‐economical Lewis acid catalyzed process (see scheme, TMSOTf=trimethylsilyl trifluoromethanesulfonate). The method has been ge...

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Veröffentlicht in:Angewandte Chemie International Edition 2003-05, Vol.42 (21), p.2389-2392
Hauptverfasser: Renard, Pierre-Yves, Vayron, Philippe, Leclerc, Eric, Valleix, Alain, Mioskowski, Charles
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Sprache:eng
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Zusammenfassung:The taming of the shrew! For the first time, a broadly applicable efficient room‐temperature Arbuzov rearrangement is described. This reaction is accomplished through an atom‐economical Lewis acid catalyzed process (see scheme, TMSOTf=trimethylsilyl trifluoromethanesulfonate). The method has been generalized to primary and activated secondary phosphites, phosphinites, and phosphonites.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200250270