Article
Chemistry, Organic
Shelby M. Anderson, Marcus D. Van Engen, Paul E. Floreancig
Summary: The sequential allylic alcohol transposition, carbonyl group trapping, oxocarbenium ion formation, and nucleophilic addition result in ring formation and serve as a fragment-coupling and stereocenter-generating reaction. Balancing the kinetics of productive and unproductive steps is crucial for successful applications, and solvent changes can be used to expand the scope and change the stereochemical outcomes of the processes. Mechanistic studies provide insight into the transformations and reactive species generated.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xufang Liu, Xianle Rong, Shihan Liu, Yu Lan, Qiang Liu
Summary: A novel method for the synthesis of chiral cyclic olefins, specifically 1-methylcyclohexenes, was reported in this study, enabling the construction of chiral compounds with diversified functionalities. The synthetic utility of this method was demonstrated by the concise and enantioselective synthesis of a natural product, beta-bisabolene, and further derivatizations showcased the versatility of the reaction products.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Qiulin You, Xin Xiao, Yang Shi, Yimin Wu, Guangying Tan
Summary: This study reveals a novel iron-catalyzed para-C-H allylation reaction of aniline derivatives via a chelation-induced strategy, providing various allylic arenes with good yields and selectivity.
Article
Chemistry, Organic
Qiulin You, Xin Xiao, Yang Shi, Yimin Wu, Guangying Tan
Summary: Transition-metal-catalyzed directed C-H allylation of arenes is an efficient method to construct value-added allylic arenes. This study presents a novel iron catalyst and a chelation-induced strategy for the para-C-H allylation of aniline derivatives, which provides good yields and excellent selectivity.
Article
Chemistry, Multidisciplinary
Jiaming Liu, Ming Chen
Summary: A Rhenium-catalyzed stereoselective transposition of allylic alcohols is described. In the presence of 1 mol% of Re2O7, (E)- or (Z)-δ-hydroxymethyl-anti-homoallylic alcohols were converted into the acetals of 2-methyl-1,3-syn-diols with excellent diastereoselectivities. 1,3-syn-Diol acetals can also be synthesized from (E)-δ-hydroxymethyl-syn-homoallylic alcohols.
Article
Chemistry, Multidisciplinary
Xingben Wang, Frederic W. Patureau
Summary: The highly selective synthesis of mono- and di-2-fluoroallylic amines from gem-difluorocyclopropanes and primary anilines using a Pd catalyst is described. Initial kinetic studies suggest a first order reaction with the gem-difluorocyclopropane substrate and a zeroth order reaction with the aniline coupling partner. The newly synthesized fluoroallylic motifs have important applications in synthetic and medicinal chemistry, and can potentially stimulate the development of coupling methods using strained cyclic building blocks.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Xi-Jia Liu, Wen-Yun Zhang, Chao Zheng, Shu-Li You
Summary: Herein, an Ir-catalyzed asymmetric allylic substitution reaction of methyl azaarenes is reported. The reaction exhibits high yields and enantioselectivity, and utilizes the Knochel reagent for the formation of benzylic nucleophiles without additional activating reagents. The synthetic utility of this method has been demonstrated by an enantioselective synthesis of an allosteric protein kinase modulator.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Yaru Gao, Guorong Hong, Bin-Miao Yang, Yu Zhao
Summary: Direct substitution of readily available alcohols is an important area of research in green chemical synthesis. Catalytic enantioconvergent transformations of racemic secondary alcohols are desired for efficient access to valuable enantiopure compounds. The enantioconvergent borrowing hydrogen methodology has proven to be effective for achieving such transformations. This review provides an overview of the progress made in the past decade, focusing on the conversion of racemic secondary alcohols to enantioenriched chiral amines, N-heterocycles, higher-order alcohols, and ketones.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Energy & Fuels
Lelia Cosimbescu, Kristen B. Campbell, Jotheeswari Kothandaraman, Deepika Malhotra, Marie S. Swita
Summary: This study demonstrates the formation of symmetrical and unsymmetrical allylic ethers using molybdenum catalysts for the first time. By optimizing reaction conditions, it was possible to maximize the conversion of prenol and generate the main products.
Article
Chemistry, Organic
Alessandra Casnati, Dawid Lichosyt, Bruno Lainer, Lukas Veth, Pawel Dydio
Summary: The research presents a multicatalytic method for converting alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivity. Prochiral allylic alcohols can also be selectively transformed into different stereoisomers of the product.
Article
Chemistry, Organic
Nuria Vazquez-Galinanes, Isabel Velo-Heleno, Martin Fananas-Mastral
Summary: A method for the use of vinyl epoxides in catalytic allylboration of alkynes is described, which allows for the synthesis of bifunctional skipped dienes bearing both an allylic alcohol and an alkenylboronate from simple starting materials with high regio- and stereoselectivity. These products show versatile reactivity and can be converted into cyclic boron compounds and polyenes.
Article
Chemistry, Organic
Dustin D. Youmans, Hai N. Tran, Levi M. Stanley
Summary: Nickel-catalyzed isomerizations of homoallylic alcohols and a bishomoallylic alcohol proceed efficiently without the need for an exogenous ligand. The corresponding ketones are obtained in high yields (≤98%).
Article
Chemistry, Organic
Masahiro Sai
Summary: The isomerization of allylic alcohols is an important reaction, and this paper reports the development of an efficient catalytic system that allows for the isomerization of a broad range of substrates with high yields. The catalytic system was also successfully applied to a tandem reaction.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zeng-Hua Wu, Huai-Yu Wang, Huai-Lan Yang, Li-Hua Wei, Tamio Hayashi, Wei-Liang Duan
Summary: An iridium-catalyzed asymmetric synthesis of branched allylic phosphine compounds with excellent stereoselectivity and regioselectivity is reported. The use of phosphine sulfides with low deactivation capacity is crucial for the success of this reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Masahiro Sai
Summary: This study introduces a novel base-promoted reaction method for the diastereoselective synthesis of 1,3-diols with three contiguous stereogenic centers from allylic alcohols and aldehydes via allylic isomerization-initiated Aldol-Tishchenko reactions. Unlike traditional systems, this method utilizes readily available allylic alcohols as nucleophiles instead of enolizable aldehydes and ketones, offering a more sustainable and efficient approach to complex diol synthesis.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Physical
B. Zhang, S. Kaziz, H. Li, M. G. Hevia, D. Wodka, C. Mazet, T. Buergi, N. Barrabes
JOURNAL OF PHYSICAL CHEMISTRY C
(2015)
Article
Chemistry, Multidisciplinary
Houhua Li, Clement Mazet
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Article
Chemistry, Multidisciplinary
Weilong Liu, Houhua Li, Pei-Jun Cai, Zhen Wang, Zhi-Xiang Yu, Xiaoguang Lei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Physical
Houhua Li, Daniele Fiorito, Clement Mazet
Article
Plant Sciences
Zongwei Yue, Xinhua Xiao, Jinbao Wu, Xiaozhou Zhou, Weilong Liu, Yaxi Liu, Houhua Li, Guoqiang Chen, Yingli Wu, Xiaoguang Lei
JOURNAL OF NATURAL PRODUCTS
(2018)
Article
Chemistry, Multidisciplinary
Gang Shan, Jana Flegel, Houhua Li, Christian Merten, Slava Ziegler, Andrey P. Antonchick, Herbert Waldmann
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Houhua Li, Rajesh Gontla, Jana Flegel, Christian Merten, Slava Ziegler, Andrey P. Antonchick, Herbert Waldmann
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Multidisciplinary
Benke Hong, Weilong Liu, Jin Wang, Jinbao Wu, Yuichiro Kadonaga, Pei-Jun Cai, Hong-Xiang Lou, Zhi-Xiang Yu, Houhua Li, Xiaoguang Lei
Article
Chemistry, Organic
Weilong Liu, Zongwei Yue, Zhen Wang, Houhua Li, Xiaoguang Lei
Article
Chemistry, Multidisciplinary
Yang Zhang, Yunpeng Ji, Ivan Franzoni, Chuning Guo, Hongli Jia, Benke Hong, Houhua Li
Summary: In this report, the first enantioselective total synthesis of (-)-berkeleyone A and its five congeners is presented, achieved in 12-15 steps starting from commercially available 2,4,6-trihydroxybenzoic acid hydrate. The synthesis features symmetry-breaking reactions and complex framework formation, while biomimetic investigations revealed rearrangements responsible for the diversification of (-)-berkeleyone A into its congeners.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Yunpeng Ji, Benke Hong, Ivan Franzoni, Mengyang Wang, Weiqiang Guan, Hongli Jia, Houhua Li
Summary: In this paper, a 9-step enantioselective total synthesis of (+)-hyperforin and (+)-pyrohyperforin was described, starting from commercially available allylacetone. The synthesis involved important reactions such as the enantioselective deconjugative alpha-alkylation using chiral lithium amides as stereodirecting auxiliaries, the HfCl4-mediated carbonyl alpha-tert-alkylation to form the intricate bicyclo[3.3.1]nonane framework, an abiotic cascade pyran formation, and a selective 1,4-semihydrogenation of polyenes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Saad Shaaban, Houhua Li, Felix Otte, Carsten Strohmann, Andrey P. Antonchick, Herbert Waldmann
Article
Chemistry, Multidisciplinary
Benke Hong, Dachao Hu, Jinbao Wu, Jing Zhang, Houhua Li, Yingming Pan, Xiaoguang Lei
CHEMISTRY-AN ASIAN JOURNAL
(2017)
Article
Chemistry, Multidisciplinary
Houhua Li, Xiaoguang Lei