4.8 Article

Gold(I)-catalyzed intramolecular enantioselective hydroarylation of allenes with indoles

Journal

ORGANIC LETTERS
Volume 9, Issue 10, Pages 1935-1938

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol070483c

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Funding

  1. NIGMS NIH HHS [R01 GM080422-02, R01 GM080422] Funding Source: Medline

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Treatment of 2-allenyl indole 4 with a catalytic 1:2 mixture of [(S)-2]Au2Cl2 [(S)-2 = (S)-3,5-tBu-4-MeO-MeOBIPHEP] and AgBF4 in toluene at -10 degrees C for 17 h led to isolation of tetrahydrocarbazole 5 in 88% yield with 92% ee. The protocol was effective for the cyclization of terminally disubstituted allenes and for the formation of seven-membered rings.

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