Efficient synthesis of a chiral 2-aryl Pyrrolidine

被引：0

作者：

Piper, Jared L. ^{[1
]}

Kolis, Stanley P. ^{[1
]}

Xie, Chaoyu ^{[1
]}

Bertrand, Martial ^{[2
]}

Boquel, Pascal ^{[2
]}

机构：

[1] Eli Lilly & Co, Lilly Corp Ctr, Chem Prod Res & Dev, Indianapolis, IN 46285 USA

[2] Eli Lilly & Co, Lilly Dev Ctr, Chem Prod Res & Dev SA, B-1348 Mont St Guibert, Belgium

来源：

CHIMICA OGGI-CHEMISTRY TODAY | 2012年 / 30卷 / 04期

关键词：

Asymmetric synthesis; pyrrolidine; iridium catalysts;

D O I：

暂无

中图分类号：

Q81 [生物工程学（生物技术）]; Q93 [微生物学];

学科分类号：

071005 ; 0836 ; 090102 ; 100705 ;

摘要：

2-aryl pyrrolidine 1 was efficiently prepared in three steps starting from N-vinylpyrrolidinone and ethyl 3,5-dimethylbenzoate. The key steps highlight the use of a rearrangement and an iridium catalysed hydrogenation to afford the desired compound. This methodology was utilised to prepare several differentially 2-aryl-substituted pyrrolidines in good yield and enantiomeric excess, and is complimentary to existing methods to prepare molecules of this type.

引用

页码：38 / 40

页数：3

共 50 条

[1] Synthesis and biological evaluation of a 2-aryl polyhydroxylated pyrrolidine alkaloid-based library
Tsou, En-Lun
Chen, Sih-Yu
Yang, Ming-Hsun
Wang, Shih-Chi
Cheng, Ting-Ren Rachel
Cheng, Wei-Chieh
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (24) : 10198 - 10204
[2] An efficient green protocol for the synthesis of 2-aryl substituted benzothiazoles
Mali, Jyotirling R.
Jawale, Dhanaji V.
Londhe, Balaji S.
Mane, Ramrao A.
[J]. GREEN CHEMISTRY LETTERS AND REVIEWS, 2010, 3 (03) : 209 - 212
[3] AN EFFICIENT AND MILD SYNTHESIS OF 2-ARYL BENZIMIDAZOLES IN AQUEOUS MEDIA
Sonar, Jayant P.
Pardeshi, Sandeep D.
Pawar, Shivaji S.
Thore, Shivaji N.
[J]. INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 21 (04) : 315 - 318
[4] Efficient synthesis of 2-aryl benzothiazoles mediated by Vitreoscilla hemoglobin
Xu, Yaning
Zhao, Nan
Li, Fengxi
Xie, Hanqing
Wu, Junhao
Wang, Chunyu
Li, Zhengqiang
Wang, Lei
[J]. MOLECULAR CATALYSIS, 2022, 533
[5] Efficient Palladium-Catalyzed Synthesis of 2-Aryl Propionic Acids
Neumann, Helfried
Sergeev, Alexey G.
Spannenberg, Anke
Beller, Matthias
[J]. MOLECULES, 2020, 25 (15):
[6] Magnetic Ionic Liquid [bmim][FeCl4] as an Efficient Catalyst for the Synthesis of 2-Aryl Benzimidazoles and 2-Aryl Benzothiazoles Derivatives
Sayyahi, Soheil
Shabani, Sara
Ghasemi, Sara
Azin, Atena
Hasani, Seyyed Morteza
[J]. ORIENTAL JOURNAL OF CHEMISTRY, 2015, 31 (03) : 1773 - 1778
[7] A simple and efficient mechanochemical route for the synthesis of 2-aryl benzothiazoles and substituted benzimidazoles
Banerjee, Mainak
Chatterjee, Amrita
Kumar, Vikash
Bhutia, Zigmee T.
Khandare, Dipratn G.
Majik, Mahesh S.
Roy, Biswajit Gopal
[J]. RSC ADVANCES, 2014, 4 (74) : 39606 - 39611
[8] A Rapid Synthesis of 2-Aryl Polyhydroxylated Pyrrolidines
Su, Jia-Kun
Jia, Yue-Mei
He, Ruirui
Rui, Pei-Xin
Han, Nanyin
He, Xihui
Xiang, Junfeng
Chen, Xin
Zhu, Jinghua
Yu, Chu-Yi
[J]. SYNLETT, 2010, (11) : 1609 - 1616
[9] Synthesis of novel 2-aryl AICAR derivatives
Kohyama, N
Katashima, T
Yamamoto, Y
[J]. SYNTHESIS-STUTTGART, 2004, (17): : 2799 - 2804
[10] SYNTHESIS OF 2-ARYL DERIVATIVES OF PENTABORANE(9)
HEPPERT, JA
GAINES, DF
[J]. INORGANIC CHEMISTRY, 1982, 21 (12) : 4117 - 4121

← 1 2 3 4 5 →