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| 手性的H‘4-NOBIN衍生物在不对称加成和取代反应中的应用 | |
| 引用本文： | 杜云锋,李新生,徐东成.手性的H‘4-NOBIN衍生物在不对称加成和取代反应中的应用[J].有机化学,2009,29(12):1992-1996. |
| 作者姓名： | 杜云锋 李新生 徐东成 |
| 作者单位： | 1. 浙江师范大学化学与生命科学学院,金华,321004 2. 浙江师范大学化学与生命科学学院,金华,321004;浙江师范大学物理化学研究所,浙江省固体表面反应化学重点实验室,金华,321004 |
| 摘 要： | 以手性 H’4-NOBIN为原料合成了新型手性氨基酚2和N,P配体5, 并将化合物2应用于催化二乙基锌对醛的不对称加成反应, 产率达90%, 对映体过量最高为45.9% ee. 化合物5用于钯催化的1,3-二苯基-2-烯丙基乙酸酯的不对称烯丙基烷基化反应, 产率为89%, 对映体过量最高为81.6% ee. 结果表明氨基酚2手性诱导作用弱于未氢化的NOBIN, 但却高于其八氢衍生物, 而N,P配体5给出相反的结果. |
| 关 键 词： | H‘4-NOBIN 氨基酚 二乙基锌 N P配体 烯丙基烷基化 |
| 收稿时间： | 2008-11-18 |
| 修稿时间： | 2009-04-02 |
Application of Chiral H’4-NOBIN Derivatives in Asymmetric Addition and Alkylation |
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| Du,Yunfeng,Li,Xinsheng,Xu,Dongcheng.Application of Chiral H’4-NOBIN Derivatives in Asymmetric Addition and Alkylation[J].Chinese Journal of Organic Chemistry,2009,29(12):1992-1996. | |
| Authors: | Du Yunfeng Li Xinsheng Xu Dongcheng |
| Institution: | ( Department of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004) ( Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua 321004) |
| Abstract: | Two chiral ligands (aminol and aminophosphine) derivatived from (R)-H'4-NOBIN were prepared. Chiral amino phenol 2 was employed as a catalyst in the asymmetric addition reaction of diethylzinc to aldehydes with the yield up to 90% and enantiomeric excesses up to 45.9% ee. Chiral N,P ligand 5 was examined for the asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate with up to 89% yield and up to 81.6% ee. The results showed the H'4-NOBIN derivatives provided weaker chiral inducement than the parent compound but better induction than H8-NOBIN derivatives, while the chiral N,P ligand 5 displayed opposite results. |
| Keywords: | H'_4-NOBIN HVNOBIN amino phenol diethylzinc N P ligand allylic alkylation |
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