Phosphine-Catalyzed (3+2) Annulation of δ-Acetoxy Allenoates with 2-Sulfonamidomalonate: Synthesis of Highly Substituted 3-Pyrrolines and Mechanistic Insight
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作者:
Wang, Dong
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Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, 1 Gehu Rd, Changzhou 213164, Peoples R ChinaChangzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, 1 Gehu Rd, Changzhou 213164, Peoples R China
Wang, Dong
[1
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Liu, Wei
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Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, 1 Gehu Rd, Changzhou 213164, Peoples R ChinaChangzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, 1 Gehu Rd, Changzhou 213164, Peoples R China
Liu, Wei
[1
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Hong, Yang
[1
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Tong, Xiaofeng
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Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, 1 Gehu Rd, Changzhou 213164, Peoples R ChinaChangzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, 1 Gehu Rd, Changzhou 213164, Peoples R China
Tong, Xiaofeng
[1
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机构:
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, 1 Gehu Rd, Changzhou 213164, Peoples R China
A mild and efficient synthetic protocol for 3-pyrrolines via the phosphine-catalyzed (3 + 2) annulation of (delta-acetoxy allenoates with 2-sulfonamidomalonate is reported. The asymmetric version (up to 83% ee) is also achieved by using phosphine (R)-SITCP as the catalyst. Mechanistic experiments disclose that the involved deprotonation of amide N-H and aza-addition to vinyl phosphonium might proceed in a concerted manner.
机构:
Chinese Acad Sci, Chengdu Inst Organ Chem, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Sichuan, Peoples R ChinaChengdu Univ, Inst Adv Study, Chengdu 610106, Sichuan, Peoples R China
Yang, Lei
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You, Yong
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Wang, Zhen-Hua
Xie, Ke-Xin
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Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Sichuan, Peoples R ChinaChengdu Univ, Inst Adv Study, Chengdu 610106, Sichuan, Peoples R China
Xie, Ke-Xin
Zhang, Xiao-Mei
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Chinese Acad Sci, Chengdu Inst Organ Chem, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Sichuan, Peoples R ChinaChengdu Univ, Inst Adv Study, Chengdu 610106, Sichuan, Peoples R China
Zhang, Xiao-Mei
Xu, Xiao-Ying
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Chinese Acad Sci, Chengdu Inst Organ Chem, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Sichuan, Peoples R ChinaChengdu Univ, Inst Adv Study, Chengdu 610106, Sichuan, Peoples R China
Xu, Xiao-Ying
Yuan, Wei-Cheng
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Chinese Acad Sci, Chengdu Inst Organ Chem, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Sichuan, Peoples R ChinaChengdu Univ, Inst Adv Study, Chengdu 610106, Sichuan, Peoples R China
机构:
Zhengzhou Univ, Coll Chem & Mol Engn, Int Phosphorus Lab, Int Joint Res Lab Funct Organophosphorus Mat Hena, Zhengzhou 450001, Henan, Peoples R ChinaZhengzhou Univ, Coll Chem & Mol Engn, Int Phosphorus Lab, Int Joint Res Lab Funct Organophosphorus Mat Hena, Zhengzhou 450001, Henan, Peoples R China
Ma, Rong
Song, Gege
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Zhengzhou Univ, Coll Chem & Mol Engn, Int Phosphorus Lab, Int Joint Res Lab Funct Organophosphorus Mat Hena, Zhengzhou 450001, Henan, Peoples R ChinaZhengzhou Univ, Coll Chem & Mol Engn, Int Phosphorus Lab, Int Joint Res Lab Funct Organophosphorus Mat Hena, Zhengzhou 450001, Henan, Peoples R China
Song, Gege
Xi, Qiuzhen
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Zhengzhou Univ, Coll Chem & Mol Engn, Int Phosphorus Lab, Int Joint Res Lab Funct Organophosphorus Mat Hena, Zhengzhou 450001, Henan, Peoples R ChinaZhengzhou Univ, Coll Chem & Mol Engn, Int Phosphorus Lab, Int Joint Res Lab Funct Organophosphorus Mat Hena, Zhengzhou 450001, Henan, Peoples R China
Xi, Qiuzhen
Yang, Liu
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Zhengzhou Univ, Coll Chem & Mol Engn, Int Phosphorus Lab, Int Joint Res Lab Funct Organophosphorus Mat Hena, Zhengzhou 450001, Henan, Peoples R ChinaZhengzhou Univ, Coll Chem & Mol Engn, Int Phosphorus Lab, Int Joint Res Lab Funct Organophosphorus Mat Hena, Zhengzhou 450001, Henan, Peoples R China
Yang, Liu
Li, Er-Qing
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Zhengzhou Univ, Coll Chem & Mol Engn, Int Phosphorus Lab, Int Joint Res Lab Funct Organophosphorus Mat Hena, Zhengzhou 450001, Henan, Peoples R ChinaZhengzhou Univ, Coll Chem & Mol Engn, Int Phosphorus Lab, Int Joint Res Lab Funct Organophosphorus Mat Hena, Zhengzhou 450001, Henan, Peoples R China
Li, Er-Qing
Duan, Zheng
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机构:
Zhengzhou Univ, Coll Chem & Mol Engn, Int Phosphorus Lab, Int Joint Res Lab Funct Organophosphorus Mat Hena, Zhengzhou 450001, Henan, Peoples R ChinaZhengzhou Univ, Coll Chem & Mol Engn, Int Phosphorus Lab, Int Joint Res Lab Funct Organophosphorus Mat Hena, Zhengzhou 450001, Henan, Peoples R China