Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes

Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes
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DOI:
10.1021/ja0762240
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发表时间:
2007-10-31
影响因子:
15
通讯作者:
Chemler, Sherry R.
Chemler, Sherry R.
中科院分区:
化学1区
文献类型:
--
作者:
Zeng, Wei;Chemler, Sherry R.

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提出了用于合成氮杂环的γ-烯基芳基磺酰胺和δ-烯基芳基磺酰胺的对映选择性氧化环化。该反应由手性铜(II)络合物催化,MnO2 被用作廉价的化学计量氧化剂。多种五元杂环和四氢异喹啉已以良好至优异的产率合成,并且具有良好至优异的对映选择性水平。这是首次报道铜催化烯烃的对映选择性碳胺化反应。
The enantioselective oxidative cyclizations of gamma-alkenyl arylsulfonamides and a delta-alkenyl arylsulfonamide for the synthesis of nitrogen heterocycles are presented. The reactions are catalyzed by chiral copper(II) complexes, and MnO2 is used as the inexpensive stoichiometric oxidant. A variety of five-membered heterocycles and a tetrahydroisoquinoline have been synthesized in good to excellent yields with good to excellent levels of enantioselectivity. This is the first reported copper-catalyzed enantioselective carboamination of alkenes.