1373340-29-4Relevant academic research and scientific papers
Asymmetric synthesis of allenyl oxindoles and spirooxindoles by a catalytic enantioselective saucy-marbet claisen rearrangement
Cao, Trung,Deitch, Joshua,Linton, Elizabeth C.,Kozlowski, Marisa C.
supporting information; experimental part, p. 2448 - 2451 (2012/04/23)
Saucy selection: The first catalytic, enantioselective Saucy-Marbet Claisen rearrangement has been achieved. Palladium(II) (R)-binap or tBuphox catalysts L*Pd(SbF6)2 were employed to generate allenyl oxindoles or spirolactones bearin
Copper(II)-and palladium(II)-catalyzed enantioselective claisen rearrangement of allyloxy-and propargyloxy-indoles to quaternary oxindoles and spirocyclic lactones
Cao, Trung,Linton, Elizabeth C.,Deitch, Joshua,Berritt, Simon,Kozlowski, Marisa C.
, p. 11037 - 11055 (2013/02/23)
In this Article, a strategy to obtain highly enantioselective catalysts for the Claisen rearrangement of allyloxy-and propargyloxy-indoles is outlined. Ultimately, copper BOX and palladium BINAP or PHOX catalysts were discovered as superior in catalyzing Claisen rearrangements of allyloxy-or proparyloxy-substituted indoles to generate oxindoles bearing allyl-or allenyl-substituted quaternary centers. This method proved to be tolerant of a broad range of functional groups. Tandem reactions of the silyl-allene products provide rapid access to a variety of spirocyclic oxindoles in one operation.
