Highly enantioselective hetero-Diels-Alder reactions between Rawal's diene and aldehydes catalyzed by chiral dirhodium(II) carboxamidates.
Highly enantioselective hetero-Diels-Alder reactions between Rawal's diene and aldehydes catalyzed by chiral dirhodium(II) carboxamidates.
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DOI：
10.1039/b919535a
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发表时间：
2009-11
影响因子：
4.9
通讯作者：
Yudai Watanabe;Takuya Washio;N. Shimada;M. Anada;S. Hashimoto*
中科院分区：
文献类型：
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作者：
Yudai Watanabe;Takuya Washio;N. Shimada;M. Anada;S. Hashimoto*
描述了 1-二甲基氨基-3-甲硅烷氧基-1,3-丁二烯（拉瓦尔二烯）和醛之间的手性路易斯酸催化对映选择性杂狄尔斯-阿尔德 (HDA) 反应的第一个例子。在1 mol%四[N-苯-稠合-邻苯二甲酰基-(S)-哌啶酸]二铑(II)，Rh(2)(S-BPTPI)(4)的影响下，环加成反应干净地进行，并在用乙酰氯处理后得到相应的二氢吡喃酮，其ee高达99%。
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.