Bifunctional Organocatalysts for Enantioselective aza-Morita-Baylis-Hillman (aza-MBH) Reactions
Bifunctional Organocatalysts for Enantioselective aza-Morita-Baylis-Hillman (aza-MBH) Reactions
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DOI：
10.5059/yukigoseikyokaishi.65.1089
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发表时间：
2007-11
影响因子：
0.2
通讯作者：
S. Takizawa;Katsuya Matsui;H. Sasai
中科院分区：
文献类型：
--
作者：
S. Takizawa;Katsuya Matsui;H. Sasai
合成了（S）-3-（N-异丙基-N-3-吡啶氨基甲基）BINOL（6a）和（S）-3-[2-（二苯基膦基）苯基] BINOL（10a）两种双功能有机催化剂，用于aza-Morita-Baylis-Hillman（aza-MBH）反应。在这些催化剂中，手性布朗斯台德酸单元通过间隔基与刘易斯碱单元连接。在α，α，β-不饱和羰基化合物与N-对甲苯磺酰亚胺的碳-碳键形成反应中，酸碱基团协同作用，作为酶模拟催化剂，以高的对映选择性激活底物。
Powerful bifunctional organocatalysts, (S)-3-(N-isopropyl-N-3-pyridinylaminomethyl) BINOL (6a) and (S)-3-[2-(diphenylphosphino) phenyl] BINOL (10a), for the aza-Morita-Baylis-Hillman (aza- MBH) reaction, were developed. In these catalysts, chiral Bronsted acid units are connected with a Lewis base unit via a spacer. The acid-base moieties act cooperatively as an enzyme-mimetic catalyst to activate substrates in the carbon-carbon bond forming reaction between a, α, β-unsaturated carbonyl compounds and N-tosylimines with high enantioselectivity.