Intramolecular [3+2] Cyclocondensations of Alkenes with Indolidenes and Indolidenium Cations

Intramolecular [3+2] Cyclocondensations of Alkenes with Indolidenes and Indolidenium Cations
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DOI:
10.1021/ja508421e
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发表时间:
2014-10-29
影响因子:
15
通讯作者:
Glinkerman, Christopher M.
Glinkerman, Christopher M.
中科院分区:
化学1区
文献类型:
--
作者:
Feldman, Ken S.;Gonzalez, Inanllely Y.;Glinkerman, Christopher M.

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C(2)-C(3)环戊烷化的吲哚构建体通过(a)连接到2-叠氮基-1-联烯基苯核的链烯基硫化物的环化级联或(B)连接的链烯基硫化物与推定的2-吲哚鎓阳离子的阳离子环化来制备。在这两种情况下,C-C键与C-N键形成的问题出现,结果表明,前者是有利的。
C(2)-C(3) cyclopentannelated indole constructs are prepared by either (a) a cyclization cascade of an alkenyl sulfide tethered to a 2-azido-1-allenylbenzene core or (b) cationic cyclization of a tethered alkenyl sulfide with a putative 2-indolidenium cation. In both cases, issues of C-C versus C-N bond formation emerge, and the results indicate that the former is favored.