Theoretical Analysis of a Three-Component Reaction between Two Diazo Compounds and a Hydroxylamine Derivative: Mechanism, Enantioselectivity, and Effect of Cooperative Catalysis
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作者:
Qi, Simeng
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Shaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Key Lab Chem Addit China Natl Light Ind, Xian 710021, Peoples R ChinaShaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Key Lab Chem Addit China Natl Light Ind, Xian 710021, Peoples R China
Qi, Simeng
[1
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Ma, Ji
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Shaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Key Lab Chem Addit China Natl Light Ind, Xian 710021, Peoples R ChinaShaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Key Lab Chem Addit China Natl Light Ind, Xian 710021, Peoples R China
Ma, Ji
[1
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Yan, Guowei
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Shaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Key Lab Chem Addit China Natl Light Ind, Xian 710021, Peoples R ChinaShaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Key Lab Chem Addit China Natl Light Ind, Xian 710021, Peoples R China
Yan, Guowei
[1
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Kirillov, Alexander M.
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Univ Lisbon, Dept Engn Quim, Inst Super Tecn, Ctr Quim Estrutural,Inst Mol Sci, P-1049001 Lisbon, PortugalShaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Key Lab Chem Addit China Natl Light Ind, Xian 710021, Peoples R China
Kirillov, Alexander M.
[2
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Yang, Lizi
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Lanzhou Univ, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R ChinaShaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Key Lab Chem Addit China Natl Light Ind, Xian 710021, Peoples R China
Yang, Lizi
[3
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Fang, Ran
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Shaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Key Lab Chem Addit China Natl Light Ind, Xian 710021, Peoples R ChinaShaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Key Lab Chem Addit China Natl Light Ind, Xian 710021, Peoples R China
Fang, Ran
[1
]
机构:
[1] Shaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Key Lab Chem Addit China Natl Light Ind, Xian 710021, Peoples R China
[2] Univ Lisbon, Dept Engn Quim, Inst Super Tecn, Ctr Quim Estrutural,Inst Mol Sci, P-1049001 Lisbon, Portugal
[3] Lanzhou Univ, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China
The mechanism, enantioselectivity, and effect of chiral phosphoric acid (CPA) cocatalyst were investigated by the density functional theory (DFT) for the three-component asymmetric aminohydroxylation between two diazo compounds and a hydroxylamine derivative. This type of cascade process is cooperatively catalyzed by Rh-2(OAc)(4) and CPA. The obtained results clearly indicate that the first step of the global reaction involves a nucleophilic attack at the nitrogen center of N-hydroxyaniline by rhodium-carbene intermediates producing imines. Subsequently, an enolate intermediate was recognized as the key species generated from the second diazo compound and the leaving benzyl alcohol (BnOH) fragment of the first step and in the presence of the same dirhodium catalyst. Then, the reaction is terminated by the asymmetric Mannich-type addition, delivering the aminohydroxylation products of an S-R conformation with the assistance of chiral phosphoric acid. The distortion/interaction analysis shows that the relative distortions of CPA and the enol play a vital role in the energy ordering of the stereocontrolling transition states (TSs). Furthermore, the influence of different substituents in CPA was fully rationalized by distortion/interaction analysis. This study opens up novel synthetic possibilities and improves the reaction predictability when exploring the related types of cooperatively catalyzed organic transformations.
机构:
Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Peoples R ChinaSun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Peoples R China
Yu, Sifan
Chen, Jinzhou
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Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Peoples R ChinaSun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Peoples R China
Chen, Jinzhou
Liu, Gengxin
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Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Peoples R ChinaSun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Peoples R China
Liu, Gengxin
Lei, Jinping
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Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Peoples R ChinaSun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Peoples R China
Lei, Jinping
Hu, Wenhao
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Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Peoples R ChinaSun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Peoples R China
Hu, Wenhao
Qiu, Huang
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Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Peoples R ChinaSun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Peoples R China
机构:
Wenzhou Univ, Dept Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
Univ Illinois, Dept Chem, 845 West Taylor St, Chicago, IL 60607 USAWenzhou Univ, Dept Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
Chen, Fa-Jie
Mamidipalli, Phani
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Univ Illinois, Dept Chem, 845 West Taylor St, Chicago, IL 60607 USAWenzhou Univ, Dept Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
Mamidipalli, Phani
Sabbasani, Venkata Reddy
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Univ Illinois, Dept Chem, 845 West Taylor St, Chicago, IL 60607 USAWenzhou Univ, Dept Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
Sabbasani, Venkata Reddy
Liu, Huaqing
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Univ Illinois, Dept Chem, 845 West Taylor St, Chicago, IL 60607 USAWenzhou Univ, Dept Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
Liu, Huaqing
Xia, Yuanzhi
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Wenzhou Univ, Dept Coll Chem & Mat Engn, Wenzhou 325035, Peoples R ChinaWenzhou Univ, Dept Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
Xia, Yuanzhi
Lee, Daesung
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Univ Illinois, Dept Chem, 845 West Taylor St, Chicago, IL 60607 USAWenzhou Univ, Dept Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
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East China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R ChinaEast China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
Xiao, Guolan
Ma, Chaoqun
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East China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R ChinaEast China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
Ma, Chaoqun
Wu, Xiang
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East China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R ChinaEast China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
Wu, Xiang
Xing, Dong
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East China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R ChinaEast China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
Xing, Dong
Hu, Wenhao
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East China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510275, Guangdong, Peoples R ChinaEast China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
机构:E China Normal Univ, Adv Res Ctr Drug Discovery & Dev, Shanghai 200062, Peoples R China
Zhu, Yingguang
Zhai, Changwei
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机构:E China Normal Univ, Adv Res Ctr Drug Discovery & Dev, Shanghai 200062, Peoples R China
Zhai, Changwei
Yue, Yongli
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机构:E China Normal Univ, Adv Res Ctr Drug Discovery & Dev, Shanghai 200062, Peoples R China
Yue, Yongli
Yang, Liping
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机构:E China Normal Univ, Adv Res Ctr Drug Discovery & Dev, Shanghai 200062, Peoples R China
Yang, Liping
Hu, Wenhao
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E China Normal Univ, Adv Res Ctr Drug Discovery & Dev, Shanghai 200062, Peoples R ChinaE China Normal Univ, Adv Res Ctr Drug Discovery & Dev, Shanghai 200062, Peoples R China
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East China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R ChinaEast China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
Xiao, Guolan
Ma, Chaoqun
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East China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R ChinaEast China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
Ma, Chaoqun
Xing, Dong
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East China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R ChinaEast China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
Xing, Dong
Hu, Wenhao
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East China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R ChinaEast China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China