Application of Chiral H’4-NOBIN Derivatives in Asymmetric Addition and Alkylation

Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (12): 1992-1996. Previous Articles Next Articles

Notes

手性的H‘4-NOBIN衍生物在不对称加成和取代反应中的应用

杜云锋^a；李新生^*,a,b；徐东成^a,b

(a浙江师范大学化学与生命科学学院金华 321004)
(b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)

收稿日期:2008-11-18 修回日期:2009-04-02 发布日期:2009-07-07
通讯作者: 李新生 E-mail:sky33@zjnu.cn
基金资助:
国家级.国家自然科学基金

Application of Chiral H’4-NOBIN Derivatives in Asymmetric Addition and Alkylation

Du, Yunfeng^a；Li, Xinsheng^*,a,b；Xu, Dongcheng^a,b

(^a Department of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004)
(^b Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua 321004)

Received:2008-11-18 Revised:2009-04-02 Published:2009-07-07

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.

Key words: H‘4-NOBIN, amino phenol, diethylzinc, N,P ligand, allylic alkylation

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DU Yun-Feng, LI Xin-Sheng, XU Dong-Cheng. Application of Chiral H’4-NOBIN Derivatives in Asymmetric Addition and Alkylation[J]. Chin. J. Org. Chem., 2009, 29(12): 1992-1996.

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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

Application of Chiral H’4-NOBIN Derivatives in Asymmetric Addition and Alkylation

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