1,4-Rhodium-Silicon Shift in an Enantioselective Synthesis of Indanols

Significance

The tendency of rhodium and palladium catalysts to undergo 1,4-shifts from alkyl or vinyl to aryl positions is a well-documented phenomenon (see Review). In contrast to their earlier work (Angew. Chem. Int. Ed. 2009, 48, 6320), the authors describe a 1,4-rhodium-silicon shift. This strategy is superior to the rhodium-hydrogen shift in the sense that functionality is introduced at the alkyl position, which can be easily further modified.

Review: F. Shi, R. C. Larock Top. Curr. Chem. 2010, 292, 123-164.