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

Gold(I)-catalyzed intramolecular enantioselective hydroarylation of allenes with indoles
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DOI:
10.1021/ol070483c
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发表时间:
2007-05-10
期刊:
影响因子:
5.2
通讯作者:
Widenhoefer, Ross A.
Widenhoefer, Ross A.
中科院分区:
化学1区
文献类型:
--
作者:
Liu, Cong;Widenhoefer, Ross A.

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2-联烯基吲哚4与[(S)-2-氯代金][(S)-2 =(S)-3,5-tBu-4-MeO-MeOBIPHEP]和AgBF 4的1:2混合物在甲苯中于-10 ℃反应17 h,得到四氢咔唑5,产率88%,ee值92%,2-联烯基吲哚4的环化反应和七元环的形成是有效的。
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.