Enantioselective Reactions of Donor/Acceptor Carbenoids Derived from α-Aryl-α-Diazoketones

Enantioselective Reactions of Donor/Acceptor Carbenoids Derived from α-Aryl-α-Diazoketones
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DOI:
10.1021/ol802614j
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发表时间:
2009-02-19
期刊:
影响因子:
5.2
通讯作者:
Davies, Huw M. L.
Davies, Huw M. L.
中科院分区:
化学1区
文献类型:
--
作者:
Denton, Justin R.;Davies, Huw M. L.

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α-芳基-a-重氮酮与活性烯烃的反应,在金刚烷基甘氨酸衍生的镝配合物Rh-2(S-PTAD)(4)的催化下,生成了具有高非对映选择性(高达>95:5dr)和对映体选择性(高达98%ee)的环丙基酮。通过类卡宾诱导的C-H插入,1,4-环己二烯的分子间C-H官能化也是可能的。
The reaction of a variety of a-aryl-a-diazo ketones with activated olefins, catalyzed by the adamantyl glycine-derived dirhodium complex Rh-2(S-PTAD)(4), generates cyclopropyl ketones with high diastereoselectivity (up to >95:5 dr) and enantioselectivity, (up to 98% ee). Intermolecular C-H functionalization of 1,4-cyclohexadiene by means of carbenoid-induced C-H insertion was also possible with this type of carbenoid.