Regio- and stereoselective Ni-catalyzed 1,4-hydroboration of 1,3-dienes: access to stereodefined (Z)-allylboron reagents and derived allylic alcohols.

Regio- and stereoselective Ni-catalyzed 1,4-hydroboration of 1,3-dienes: access to stereodefined (Z)-allylboron reagents and derived allylic alcohols.
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DOI:
10.1021/ja910750b
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发表时间:
2010-03-03
影响因子:
15
通讯作者:
Morken JP
Morken JP
中科院分区:
化学1区
文献类型:
--
作者:
Ely RJ;Morken JP

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在Ni(cod)2和PCy 3存在下,用频哪醇硼烷催化1,3-二烯的区域和立体选择性1,4-硼氢化反应。该反应表现出对一系列取代二烯进行操作的宽底物范围,并且通常以高水平的选择性和效率发生。反应模式表明,反应构象的二烯是theS-cis形式。中间体烯丙基硼酸酯可被氧化成立体定向的烯丙醇或可用于立体选择性羰基加成反应。
A catalytic regio- and stereoselective 1,4-hydroboration of 1,3-dienes was accomplished with pinacolborane in the presence of Ni(cod)2and PCy3. This reaction exhibits broad substrate scope operating on a range of substituted dienes and occurs with generally high levels of selectivity and efficiency. Reactivity patterns suggest that the reactive conformation of the diene is theS-cis form. The intermediate allylboronate can be oxidized to stereodefined allylic alcohols or can be used in stereoselective carbonyl addition reactions.
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