Nickel-catalyzed addition of dimethylzinc to aldehydes across alkynes and 1,3-butadiene: An efficient four-component connection reaction
Nickel-catalyzed addition of dimethylzinc to aldehydes across alkynes and 1,3-butadiene: An efficient four-component connection reaction
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DOI：
10.1021/ja0469030
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发表时间：
2005-01-12
影响因子：
15
通讯作者：
Tamaru, Y
中科院分区：
文献类型：
--
作者：
Kimura, M;Ezoe, A;Tamaru, Y
在10摩尔%的Ni（acac）（2）存在下，包括Me 2 Zn、炔、1，3-丁二烯和羰基化合物的四种组分以1：1：1：1的比例依次组合联合收割机，以良好的产率提供（3E，6-7）-辛二烯-1-醇1。类似地，Me 2 Zn、1，ω-二烯炔5和羰基化合物的偶联反应以良好的产率和相对于环烷烃次甲基碳和C2侧链的含OH碳的优异水平的1，5-非对映选择性来取代1-亚烷基-2-（4 ′-羟基-（1 ′ E）-烯基）环戊烷和环己烷6及其氧和氮杂环衍生物。该反应在大多数情况下在室温下在氮气下在1小时内完成，容许酯、羟基、烯丙基和炔丙基醚、烯丙基氨基和吡啶基官能团，并容纳各种芳族和脂族炔和羰基（醛和酮）。
In the presence of 10 mol % of Ni(acac)(2), four components comprising Me2Zn, alkynes, 1,3butadiene, and carbonyl compounds combine in this order in 1:1:1:1 ratio to furnish (3E,6-7)-octadien-1-ols 1 in good yields. Similarly, the coupling reaction of Me2Zn, 1,omega-dienynes 5, and carbonyls furnishes 1-alkylidene-2-(4'-hydroxy-(1'E)-alkenyl)cyclopentanes and -cyclohexanes 6 and their oxygen and nitrogen heterocycle derivatives in good yield and an excellent level of 1,5-diastereoselectivity with respect to the cycloalkane methine carbon and the OH-bearing carbon of the C2 side chain. The reaction is completed in most cases within 1 h at room temperature under nitrogen, tolerates an ester, a hydroxy, an allyl and propargyl ethers, an allylamino, and a pyridyl functionalities, and accommodates a variety of aromatic and aliphatic alkynes and carbonyls (alclehydes and ketones).