Application of a C2-symmetric copper carbenoid in the enantioselective hydrosilylation of dialkyl and aryl-alkyl ketones.

Application of a C2-symmetric copper carbenoid in the enantioselective hydrosilylation of dialkyl and aryl-alkyl ketones.
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C2对称铜carbenoid在二烷基和芳基 - 烷基酮的对映选择性水硅烷化中的应用。

DOI:
10.1021/ja209187a
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发表时间:
2011-12-14
影响因子:
15
通讯作者:
Gawley, Robert E.
Gawley, Robert E.
中科院分区:
化学1区
文献类型:
--
作者:
Albright, Abigail;Gawley, Robert E.

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我们报告了C2对称铜结合N-杂环卡宾(NHC)在多种结构不同的酮的硅氢加成反应中具有出色的反应性和对映选择性。该催化剂在还原2-丁酮和3-己酮等具有挑战性的底物时表现出非凡的对映选择性。即使在低催化剂负载量(2.0mol%)下,反应在室温下在一小时内发生,并且除了催化剂和溶剂去除之外通常不需要纯化。这种转变的范围进行了研究,在10个芳基-烷基和烷基-烷基酮的还原。
We report excellent reactivity and enantioselectivity of a C2-symmetric copper-bound N-heterocyclic carbene (NHC) in the hydrosilylation of a variety of structurally diverse ketones. This catalyst exhibits extraordinary enantioselctivity in the reduction of such challenging substrates as 2-butanone and 3-hexanone. Even at low catalyst loading (2.0 mol%) the reactions occur in under an hour at room temperature and often do not require purification beyond catalyst and solvent removal. The scope of this transformation was investigated in the reduction of ten aryl-alkyl and alkyl-alkyl ketones.
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