Palladium-catalyzed enantioselective diboration of prochiral allenes

Palladium-catalyzed enantioselective diboration of prochiral allenes
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DOI:
10.1021/ja044167u
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发表时间:
2004-12-22
影响因子:
15
通讯作者:
Morken, JP
Morken, JP
中科院分区:
化学1区
文献类型:
--
作者:
Pelz, NF;Woodward, AR;Morken, JP

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钯催化的前手性联烯的二硼化反应只发生在内部位置,并在刘易斯碱性配体结构的存在下显着加速。在初步观察的基础上,使用了手性配体,发现各种二硼化产物的对映体过量在86 - 92%ee的范围内。手性二硼反应产物应该在有机合成中有用,初步实验表明它们可能参与具有高水平手性转移的烯丙基化反应。
Pd-catalyzed diboration of prochiral allenes occurs exclusively at the internal position and is remarkably accelerated in the presence of Lewis basic ligand structures. On the basis of preliminary observations, a chiral ligand was employed, and the enantiomeric excess of a variety of diboration products was found to be in the range of 86−92% ee. The chiral diboron reaction products should be useful in organic synthesis, and preliminary experiments suggest that they may participate in allylation reactions with a high level of chirality transfer.