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, 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
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, 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, Physical
Jinguo Long, Shaomiao Xia, Ting Wang, Gui-Juan Cheng, Xianjie Fang
Summary: A regiodivergent cyanation of allylic alcohols under nickel catalysis was reported in this study, leading to the successful synthesis of challenging branched products. Dinitriles can also be obtained in good yields with high selectivity through subsequent hydrocyanation, which can be further functionalized into various compounds. Density functional theory (DFT) calculations provided insights into the role of ligands in tuning regioselectivity and reactivity.
Article
Chemistry, Organic
Chun-Tai Hung, Chun-Wei Lu, Shi-Han Huang, Yin-Feng Lu, Hsiang-Chi Chou, Cheng-Che Tsai
Summary: This research utilizes chiral sulfinamides as nucleophiles in intramolecular allylic substitution and sequential aerobic oxidation with aza-Michael addition reactions, achieving good yields of chiral isoindolines and high diastereoselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Masahiro Sai, Hiroaki Kurouchi
Summary: In this study, the first KHMDS-catalyzed Michael additions of allylic alcohols to alpha,beta-unsaturated amides were reported. The reaction proceeds smoothly with only 5 mol% of KHMDS to afford a variety of 1,5-ketoamides in high yields. Mechanistic investigations revealed that the in-situ generation of the enolate from the allylic alcohol through a tunneling-assisted 1,2-hydride shift is crucial for the success of this transformation.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Physical
Anding Li, Nan Zheng, Kai Guo, Zhongchao Zhang, Zhen Yang
Summary: This study presents a practical and environmentally friendly electrocatalytic isomerization reaction that converts allylic alcohols to corresponding carbonyl compounds without the need for external chemical oxidants and metal catalysts. The reaction demonstrates a broad substrate scope and allows for the synthesis of diverse beta-aryl ketones.
Article
Chemistry, Applied
Belen Lopez-Sanchez, Ana Belen Bohome-Espinosa, Franco Scalambra, Antonio Romerosa
Summary: The complex [RuCp(H2O-kappa O)(mPTA)(2)](CF3SO3)(3)center dot MeOH (4 center dot MeOH) was synthesized and its crystal structure determined by X-ray diffraction. The catalytic activity of 4 for the redox isomerization of 2-cyclohexen-1-ol into cyclohexanone was studied in different systems, with the highest conversion rate achieved in biphasic water/cyclohexane. The aqueous phase containing 4 was recycled up to 7 consecutive runs without significant losses of catalyst.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
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, Organic
Paresh R. Athawale, Vishal M. Zade, Gamidi Rama Krishna, D. Srinivasa Reddy
Summary: A reliable method for enone transposition using silyl group masking was developed. The method highlights enantio-switching, substituent shuffling, and Z-selectivity. It was successfully applied for the total synthesis of peribysin D and claimed for the formal synthesis of E-guggulsterone and E-volkendousin.
Article
Chemistry, Organic
Wenbo Liu, Yushan Zheng, Yihui Mao, Jieping Chen, Xiang Ren, Zhaoyang Cheng, Zhan Lu
Summary: A cobalt-catalyzed desymmetrizing isomerization of exocyclic alkenes to generate chiral 1-methylcyclohexene derivatives with good yields and enantioselectivities was reported. A novel chiral thiazolinyl iminoquinoline ligand and its cobalt complex were designed and synthesized to control the establishment of tertiary or quaternary carbon centers at a remote position. This protocol is operationally simple, and a model for the stereochemical outcome has been proposed.
Article
Chemistry, Organic
Jiantao Fu, Zoe Vaughn, Andrew F. Nolting, Qi Gao, Dexi Yang, Christopher H. Schuster, Dipannita Kalyani
Summary: This manuscript presents the development of a diastereoselective intermolecular synthesis method for alkyl ethers using reductive etherification of various ketones or aldehydes with alcohols. The key aspect of this development is the utilization of low-temperature high-throughput experimentation (HTE) technologies for rapid reaction optimization and parallel synthesis. By carefully selecting the reductant, the diastereoselectivity of this transformation can be easily controlled.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Hiroyoshi Takamura, Yuki Sugitani, Ryohei Morishita, Isao Kadota
Summary: The first total synthesis of scabrolide F, a norcembranolide isolated from Sinularia scabra, a soft coral, is described. The key synthetic intermediate, hydroxycarboxylic acid, was synthesized in a convergent manner by fragment coupling. The obtained hydroxycarboxylic acid was then subjected to macrolactonization and subsequent transannular RCM to obtain scabrolide F. This synthetic protocol can be extended to the total synthesis of other norcembranolides.
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, Physical
B. Zhang, S. Kaziz, H. Li, M. G. Hevia, D. Wodka, C. Mazet, T. Buergi, N. Barrabes
JOURNAL OF PHYSICAL CHEMISTRY C
(2015)
Review
Chemistry, Multidisciplinary
Houhua Li, Clement Mazet
ACCOUNTS OF CHEMICAL RESEARCH
(2016)
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