Article
Chemistry, Organic
Arindam Maity, Mintu Munda, Sovan Niyogi, Nivesh Kumar, Alakesh Bisai
Summary: A general strategy for asymmetric synthesis of hexahydropyrrolo[2,3-b]indole alkaloids with vicinal quaternary-tertiary centers has been disclosed via Pd(0)-catalyzed N-deacylative allylations. Asymmetric total syntheses of pseudophrynamines have been achieved using this strategy.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Song Xi, Yan Jiang, Jiaojiao Yang, Jiao Yang, Dingyin Miao, Baoyi Chen, Wanqiu Huang, Ling He, Hanyue Qiu, Min Zhang
Summary: A sequence of reactions has been developed to synthesize bicyclic indolizidines with bridgehead aza-quaternary stereocenters from chiral cyclopropyl ketones. The reactions proceed with excellent chirality transfer, tolerating various functional groups and producing products with high enantiomeric purities.
Article
Chemistry, Organic
Marvin Fresia, Thomas Lindel
Summary: The synthesis of ABCD tetracyclic partial structures of fungal indole diterpenes janthitrem B, JBIR-137, and shearinine G is reported, starting from 5-formylated indoline coupled to a dihydropyran moiety via Prins cyclization. The hydroxylated tetracyclic western half of janthitrem B was obtained in eight steps with a 10% overall yield. Alternative approaches using alkynylated precursors, including gold-catalyzed cycloisomerization, were also discussed.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Shuyuan Yang, Linger Li, Junling Zhao
Summary: A chemo- and enantioselective protocol for the N-alkylation of indoles with imines using a BINOL-derived phosphoric acid catalyst was developed. The process afforded acyclic aminals of indoles with high yields and enantioselectivity. Moreover, this method showed high efficiency for the late-stage functionalization of a bioactive compound.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Physical
You-Dong Shao, Dao-Juan Cheng
Summary: Chiral phosphoric acid catalysis has witnessed significant development in the past two decades, with successful attempts in synthesizing enantioenriched axially chiral compounds through various strategies. This review highlights the advances in atropisomeric heterocycles construction enabled by chiral phosphoric acid catalysis, aiming to motivate continuous interest in atroposelective reactions.
Article
Chemistry, Organic
Jin-xin Zhu, Jin-Miao Tian, Yao-Yao Chen, Xue-Jiao Hu, Xue Han, Wenchao Chen, Zhikun Yang, Xiaoze Bao, Xinyi Ye, Hua Chen, Fu-Min Zhang, Hong Wang, Yong-Qiang Tu
Summary: An asymmetric [3+2] cycloaddition reaction between quinone esters and 2,3-dihydrofuran has been successfully achieved using a newly developed Cu(II)/SPDO complex. This reaction provides a straightforward route for the synthesis of 2,3,3a,8a-tetrahydrofuro[2,3-b]benzofurans with high enantioselectivity and diastereoselectivity. The resulting compounds contain two adjacent stereocenters and a continuously functionalized benzene ring. The reaction can be easily scaled up and used for the expedient synthesis of specific natural compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Applied
Yuxue Cao, Guodu Liu
Summary: Chiral phosphoric acid has been a crucial catalyst in chemical synthesis for over five decades. However, a revolutionary approach using photocatalytic excitation of molecules to generate free radicals has emerged in recent years, surpassing the limitations of traditional organic synthesis methods. A significant area of research focuses on chiral phosphoric acid synergistic photocatalysis for enantioselective chemical synthesis, utilizing a bifunctional hydrogen-bonding catalyst.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Matthew J. J. Genzink, Matthew D. D. Rossler, Herman Recendiz, Tehshik P. P. Yoon
Summary: Chiral acid catalysts are shown to promote highly selective visible-light photocycloadditions, leading to the synthesis of truxinate natural products. This general approach allows for the efficient synthesis of dimeric and pseudodimeric cyclobutane natural products with excellent enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Xufeng Lin, Lei Wang, Zhao Han, Zhouli Chen
Summary: Chiral spirocyclic phosphoric acids (SPAs) introduced in 2010 are versatile catalysts for a wide range of asymmetric organocatalytic reactions, with applications in metal-organic cooperative catalysis, organic photoredox catalysis, total synthesis, materials science, and molecular recognition. This account summarizes the past decade's advances in this field, highlighting significant achievements.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jun Kee Cheng, Bin Tan
Summary: This article introduces the wide applications and importance of indole compounds in designing new axially chiral scaffolds. The rich reactivity and N-H functionality of indole compounds allow chemical derivatization for enhanced medicinal, material, and catalytic properties. The research group successfully synthesized chiral biaryl compounds through the design of novel organocatalytic arylation reactions. Indole compounds showed reliable reactivity with azoarenes, nitrosonapthalenes, and quinone derivatives, which, in combination with chiral phosphoric acid catalyst, enabled excellent control of stereo-, chemo-, and regioselectivity to furnish diverse scaffolds. Additionally, indole compounds can also act as nucleophiles in the desymmetrization of 1,2,4-triazole-3,5-diones. This account provides a succinct illustration of these developments.
Article
Chemistry, Multidisciplinary
Rui Yang, Zeyu Zhou, Huanfeng Jiang, Toh-Seok Kam, Kai Chen, Zhiqiang Ma
Summary: The first asymmetric total synthesis of the monoterpenoid indole alkaloid arboduridine has been achieved. The synthesis involves several reactions to construct the complex structure and demonstrates a highly enantioselective synthetic strategy.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Xin-Wei Wang, Xiang Li, Mu-Wang Chen, Bo Wu, Yong-Gui Zhou
Summary: Chiral phosphoric acid-catalyzed Pictet-Spengler reactions have been successfully employed to synthesize a series of novel compounds with excellent yields and high enantiomeric excess.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Guanqun Zhan, Fuxin Zhang, Kailing Yang, Tao Yang, Ruixi Zhou, Xueqing Ma, Nan Wang, Zengjun Guo
Summary: A new compound and four known compounds were isolated from Alstonia scholaris. The new compound has a unique carbon skeleton and shows potential anti-inflammatory activity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Biki Ghosh, Reena Balhara, Garima Jindal, Santanu Mukherjee
Summary: The first catalytic enantioselective Fischer indolization of prochiral diketones containing enantiotopic carbonyl groups is developed through dynamic kinetic resolution. Catalyzed by a combination of a spirocyclic chiral phosphoric acid and ZnCl2, this approach efficiently synthesizes cyclopenta[b]indole derivatives with an all-carbon quaternary stereocenter in good to excellent enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Kang Dong, Jia Li, Rui-Peng Li, Mingming Mao, Jian Liu, Xiaolei Wang, Shouchu Tang
Summary: A simple and efficient method for synthesizing structurally diverse symmetrical and unsymmetrical 3,3'- and 2,3'-bisindolylmethanes has been developed using a one-pot sequential reaction with 1,3-dithiane as the methylene source. The important AhR agonists ICZ and malassezin were successfully synthesized with excellent efficiency using this straightforward approach.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ya-Yi Wang, Kyohei Kanomata, Toshinobu Korenaga, Masahiro Terada
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Multidisciplinary
Zhi-Yong Han, Dian-Feng Chen, Ya-Yi Wang, Rui Guo, Pu-Sheng Wang, Chao Wang, Liu-Zhu Gong
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2012)
Article
Chemistry, Multidisciplinary
Ya-Yi Wang, Jeffrey W. Bode
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)