On-step synthesis of a bifunctional BINOL ligand for the highly enantioselective cyanation of aliphatic aldehydes.

On-step synthesis of a bifunctional BINOL ligand for the highly enantioselective cyanation of aliphatic aldehydes.
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DOI:
10.1021/ol050660e
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发表时间:
2005-05
期刊:
影响因子:
5.2
通讯作者:
Ying‐chuan Qin;Lan Liu;L. Pu
Ying‐chuan Qin;Lan Liu;L. Pu
中科院分区:
化学1区
文献类型:
--
作者:
Ying‐chuan Qin;Lan Liu;L. Pu

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[反应:见正文]已经开发了光学活性双官能BINOL配体(S)-3的有效一步合成。结果表明,(S)-3与Me_2AlCl的配合物对TMSCN与不同结构的脂肪醛的加成反应具有很高的对映选择性,也是最实用的催化剂之一。发现该手性配体具有显著的正非线性效应。
[reaction: see text] An efficient one-step synthesis of the optically active bifunctional BINOL ligand (S)-3 has been developed. It was found that (S)-3 in combination with Me2AlCl is a highly enantioselective catalyst for the addition of TMSCN to aliphatic aldehydes of diverse structures and is also among the most practical ones. A remarkable positive nonlinear effect was found for this chiral ligand.