Gold(I)-catalyzed dearomative Rautenstrauch rearrangement: enantioselective access to cyclopenta[b]indoles.

A highly enantioselective dearomative Rautenstrauch rearrangement catalyzed by cationic (S)-DTBM-Segphosgold(I) is reported. This reaction provides a straightforward method to prepare enantioenriched cyclopenta[b]indoles. These studies show vast difference in enantioselectivity in the reactions of propargyl acetates and propargyl acetals in the chiral ligand-controlled Rautenstrauch reaction.

Citation

Weiwei Zi, Hongmiao Wu, F Dean Toste. Gold(I)-catalyzed dearomative Rautenstrauch rearrangement: enantioselective access to cyclopenta[b]indoles. Journal of the American Chemical Society. 2015 Mar 11;137(9):3225-8

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PMID: 25710515

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