Synthesis of Chiral Amides Emodying the Bispidine Framwork and Their Application in 1,4-Addition Reaction

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (04): 497-504. Previous Articles Next Articles

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手性双哌啶酰胺的合成及在共轭加成中的应用

石乃月，高敬园，张月成*，赵继全

(河北工业大学化工学院天津 300130)

收稿日期:2010-07-15 修回日期:2010-09-26 发布日期:2010-11-23
通讯作者: 张月成 E-mail:yczhang@hebut.edu.cn

Synthesis of Chiral Amides Emodying the Bispidine Framwork and Their Application in 1,4-Addition Reaction

SHI Nai-Yue, GAO Jing-Yuan, ZHANG Yue-Cheng, ZHAO Ji-Quan

(School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130)

Received:2010-07-15 Revised:2010-09-26 Published:2010-11-23

Abstract

3-Isopropyl-3,7-diazabicyclo[3.3.1]nonane 9 was conveniently synthesized from N-benzyl- 4-piperidinone and isopropyl amine via double Mannich reaction, Wolff-Kishner reduction, debenzylation through Pd/C catalyzed hydrogenation. Subsequently, compound 9 was reacted with four N-tert-butoxycarbonyl-L-amino acids, followed by deprotection of tert-butoxycarbonyl group, to generate four new chiral α-amino amide ligends 12a～12d. They were used in Ni-catalyzed enantioselective 1,4-conjugate addition of diethyl zinc to α,β-unsaturated ketones. The effects of steric properties of chiral ligands, molar ratio of chiral ligand to nickel source, loading amount of ligand, solvent and temperature on 1,4-conjugate addition were investigated. Under the optimized conditions: MeCN as solvent, 12c (20 mol%) as ligand, Ni(acac)₂(7 mol%), Et₂Zn (150%), a yield of 87% and an enantioselectivity of 77% were obtained, respectively. The possible mechanism for the asymmetric addition reactions was discussed.

Key words: N-benzyl-4-piperidinone, bispidine, amino acid, diethyl zinc, chiral amide, enantioselective 1,4-conjugate addition

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SHI Nai-Yue, GAO Jing-Yuan, ZHANG Yue-Cheng, ZHAO Ji-Quan. Synthesis of Chiral Amides Emodying the Bispidine Framwork and Their Application in 1,4-Addition Reaction[J]. Chin. J. Org. Chem., 2011, 31(04): 497-504.

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手性双哌啶酰胺的合成及在共轭加成中的应用

Synthesis of Chiral Amides Emodying the Bispidine Framwork and Their Application in 1,4-Addition Reaction

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