直接、温和、通用的 n-BuNBr-催化的醛烯丙基硅烷化反应与烯丙基氯。
Direct, Mild, and General n-BuNBr-Catalyzed Aldehyde Allylsilylation with Allyl Chlorides.
机构信息
Department of Chemistry, Columbia University , New York, New York 10027, United States.
出版信息
Org Lett. 2017 Nov 3;19(21):6024-6027. doi: 10.1021/acs.orglett.7b03193.
Abstract
A direct, mild, and general method for the enantioselective allylsilylation of aldehydes with allyl chlorides is reported. The reactions are effectively catalyzed by 5 mol % of n-BuNBr, and this rate acceleration allows the use of complex allyl donors in fragment-coupling reactions and of electron-deficient allyl donors. The results are (1) significant progress toward a "universal" asymmetric aldehyde allylation reaction that can reliably and highly stereoselectively couple any allyl chloride_aldehyde combination and (2) the discovery of a novel mode of nucleophilic catalysis for aldehyde allylsilylation reactions.
摘要
报道了一种直接、温和、通用的方法，用于在醛与烯丙基氯的对映选择性烯丙基硅烷化反应中。反应在 5 mol%的 n-BuNBr 的有效催化下进行，这种速率加速使得复杂的烯丙基供体能够用于片段偶联反应和缺电子的烯丙基供体。结果是（1）朝着“通用”的不对称醛烯丙基化反应取得了显著进展，可以可靠地和高度立体选择性地偶联任何烯丙基氯-醛组合，（2）发现了一种新颖的醛烯丙基硅烷化反应的亲核催化模式。
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