Gold(I)-catalyzed enantioselective [3+2] and [3+3] cycloaddition reactions of propargyl acetals/ketals.
Gold(I)-catalyzed enantioselective [3+2] and [3+3] cycloaddition reactions of propargyl acetals/ketals.
复制标题
DOI：
10.1016/j.tet.2015.04.109
复制
发表时间：
2015-09-02
期刊：
影响因子：
2.1
通讯作者：
Toste FD
中科院分区：
文献类型：
--
作者：
Navarro C;Shapiro ND;Bernasconi M;Horibe T;Toste FD
报道了一种不对称金催化炔丙基缩醛/缩酮与醛的[3+2]环加成反应，该反应通过缩醛/缩酮的逐步迁移-断裂和原位生成的金-类卡宾中间体的环加成反应进行.以高产率和高的对映选择性合成了多种功能化的2，5-二氢呋喃。此外，第一个金（I）催化的仲炔丙基缩酮和硝酮的[3+3]环加成反应的例子。
An asymmetric gold(I)-catalyzed [3+2] cycloaddition of propargyl acetals/ketals and aldehydes is reported, which proceeds via stepwise migration-fragmentation of acetals/ketals and cycloaddition of the in situ generated gold-carbenoid intermediate. Various functionalized 2, 5-dihydrofurans were obtained in good yields and high enantioselectivities. Furthermore, an example of the first gold(I) catalyzed [3+3] cycloaddition of secondary propargyl ketals and nitrones is presented.