Organic Letters
Organic Letters
5 years ago

BF3-Promoted Divergent Reactions between Tryptophols and Propargylic Alcohols

BF3-Promoted Divergent Reactions between Tryptophols and Propargylic Alcohols
Ping Lu, Guorong Sheng, Kai Huang, Yanguang Wang
Trifluoroboron-promoted cascade reactions between tryptophols and propagylic alcohols furnished three types of skeletons, including carbazoles, cyclopenta[b]furo[2,3-b]indoles, and allenyl furo[2,3-b]indoles, with excellent selectivity based on the substrate structure. Tryptophols without a substituent on the 2-position of the indole ring reacted with 1,1,3-triphenylprop-2-yn-1-ol and 9-(phenylethynyl)-9H-fluoren-9-ol to give carbazoles and cyclopenta[b]furo[2,3-b]indoles, respectively, while the reaction of 2-substituted tryptophols afforded allenylfuro[2,3-b]indoles.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01769

DOI: 10.1021/acs.orglett.7b01769

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