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Enantioselective Allylation of Indoles: A Surprising Diastereoselectivity.
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2020-01-17 , DOI: 10.1021/acs.joc.9b02573 Patrick Ullrich 1 , Julie Schmauck 2 , Marcus Brauns 1 , Marvin Mantel 1 , Martin Breugst 2 , Jörg Pietruszka 1, 3
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2020-01-17 , DOI: 10.1021/acs.joc.9b02573 Patrick Ullrich 1 , Julie Schmauck 2 , Marcus Brauns 1 , Marvin Mantel 1 , Martin Breugst 2 , Jörg Pietruszka 1, 3
Affiliation
Herein we show a novel approach toward the allylation of indoles. Thereby, we explore a class of bench-stable allylboronates and fine-tune their reactivity. The allylations of different substituted indoles proceed with negligible diastereo- and excellent enantioselectivities. This surprising selectivity (up to 99:1 er, up to ≈60:40 dr) is rationalized by DFT calculations.
中文翻译:
吲哚的对映选择性烯丙基化:令人惊讶的非对映选择性。
在这里,我们显示了一种新颖的方法来使吲哚烯丙基化。因此,我们探索了一类稳定的烯丙基硼酸酯,并对其反应性进行了微调。不同取代的吲哚的烯丙基化具有可忽略的非对映异构性和优异的对映选择性。这种令人惊讶的选择性(高达99:1 er,高达≈60:40 dr)通过DFT计算得以合理化。
更新日期:2020-01-17
中文翻译:
吲哚的对映选择性烯丙基化:令人惊讶的非对映选择性。
在这里,我们显示了一种新颖的方法来使吲哚烯丙基化。因此,我们探索了一类稳定的烯丙基硼酸酯,并对其反应性进行了微调。不同取代的吲哚的烯丙基化具有可忽略的非对映异构性和优异的对映选择性。这种令人惊讶的选择性(高达99:1 er,高达≈60:40 dr)通过DFT计算得以合理化。