手性双铑(II)羧酰胺催化 Rawal 二烯与醛的高对映选择性杂 Diels-Alder 反应。
Highly enantioselective hetero-Diels-Alder reactions between Rawal's diene and aldehydes catalyzed by chiral dirhodium(II) carboxamidates.
机构信息
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.
出版信息
Chem Commun (Camb). 2009 Dec 21(47):7294-6. doi: 10.1039/b919535a. Epub 2009 Oct 15.
The first example of a chiral Lewis acid-catalyzed enantioselective hetero-Diels-Alder (HDA) reaction between 1-dimethylamino-3-silyloxy-1,3-butadiene (Rawal's diene) and aldehydes is described. The cycloaddition reaction under the influence of 1 mol% of dirhodium(II) tetrakis[N-benzene-fused-phthaloyl-(S)-piperidinonate], Rh(2)(S-BPTPI)(4), proceeded cleanly and gave, after treatment with acetyl chloride, the corresponding dihydropyranones in up to 99% ee.
首次描述了手性路易斯酸催化的醛与 1-二甲氨基-3-硅氧基-1,3-丁二烯（Rawal 二烯）之间的对映选择性杂 Diels-Alder（HDA）反应。在 1 mol% 的二钌（II）四[N-苯并稠合-邻苯二甲酰基-(S)-哌啶酮]，Rh(2)(S-BPTPI)(4)的影响下，环加成反应顺利进行，在用乙酰氯处理后，以高达 99%的对映选择性得到相应的二氢吡喃酮。
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