Asymmetric Suzuki-Miyaura cross-coupling of 1-bromo-2-naphthoates using the helically chiral polymer ligand PQXphos

Asymmetric Suzuki-Miyaura cross-coupling of 1-bromo-2-naphthoates using the helically chiral polymer ligand PQXphos
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DOI:
10.1039/c5cc01074h
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发表时间:
2015-01-01
影响因子:
4.9
通讯作者:
Suginome, Michinori
Suginome, Michinori
中科院分区:
化学2区
文献类型:
--
作者:
Akai, Yuto;Konnert, Laure;Suginome, Michinori

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单手螺旋聚合物配体PQXphos在不对称Suzuki-Miyaura交叉偶联反应中合成了具有高对映选择性的轴向手性联芳酯。使用带有2,4-二甲基-3-戊基酯的溴化萘得到高产率和高对映选择性。任何一种对映体都可以通过使用单一的PQXphos通过溶剂依赖性的螺旋手性开关来选择性地合成。
A single-handed helical polymer ligand PQXphos afforded axially chiral biaryl esters with high enantioselectivities in asymmetric Suzuki-Miyaura cross-coupling. The use of naphthyl bromide bearing a 2,4-dimethyl-3-pentyl ester resulted in both high yields and high enantioselectivities. Either enantiomer could be synthesized selectively by using a single PQXphos through a solvent-dependent switch of the helical chirality.