[reaction and structure: see text] Not only axial but also helical chirality of tropos TETRAPHOS-Rh complexes can be controlled by chiral diamines. The flexibility of the TETRAPHOS-Rh complex is increased by association of DABN. In contrast, the diamine-free complex is chirally more stable than the BIPHEP counterpart. The higher levels of enantioselectivity in ene-type cyclization of 1,6-enynes can thus be achieved even at room temperature by the diamine-free TETRAPHOS-Rh complex.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol052281r | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Photoredox Catalyzed Conia-Ene-Type Cyclization/Smiles Rearrangement Cascade Reactions to Access Substituted Methylenecarbocycles.
Org Lett
September 2024
School of Chemistry, Xi'an Key Laboratory of Sustainable Energy Material Chemistry, and MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter, Xi'an Jiaotong University, Xi'an 710049, China.
Article Synopsis
- The study introduces a new photoredox-catalyzed reaction that combines Conia-ene cyclization and Smiles rearrangement using alkyne-tethered α-sulfonyl esters.
- This method enables the efficient creation of diverse and highly substituted methylenecarbocycles.
- It also reveals an innovative mechanistic pathway involving aryl group migration, which is an advancement over the traditional 1,5-hydrogen shift found in typical Conia-ene reactions.
Biomimetic total syntheses of renifolin F and antiarone K.
Org Biomol Chem
June 2024
Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, 502284, India.
The first biomimetic and concise racemic total syntheses of renifolin F and antiarone K, accomplished in 8 and 7 linear steps, respectively, are presented in this article. Our synthetic approach commences with substituted aldehydes to produce prenylated aldol products followed by ene-type intramolecular cyclization affording a five-member core ring. This key step mediated by InCl·4HO is a novel procedure first utilized in prenylated systems which directly culminates mainly into tertiary alcohols.
View Article and Find Full Text PDFSynthesis of the diazatricycloundecane scaffold gold(I)-catalysed Conia-ene-type 5- cyclization and stepwise substituent assembly for the construction of an sp-rich compound library.
Org Biomol Chem
November 2023
School of Life Science and Technology, Tokyo Institute of Technology, 4259 Nagatsuta-cho Midori-ku, Yokohama, 226-8503, Japan.
The bridged diazatricycloundecane sp-rich scaffold was synthesised the gold(I)-catalysed Conia-ene reaction. The electron-donating property of the siloxymethyl group on alkyne 1 enabled 6- cyclization, whereas the ethoxy carbonyl group on alkyne 4 led to 5- cyclization with complete regioselectivity in the Conia-ene reaction. The resulting bridged diazatricycloundecane scaffold 5 allowed the construction of a library of sp-rich compounds.
View Article and Find Full Text PDFNitroso-Ene-type Cyclization Toward Diversified Synthesis of Amino Deoxysugars: A Proof of Concept.
Org Lett
March 2023
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, People's Republic of China.
Amino deoxysugars are abundant in nature and play an important role in various biological functions, promoting numerous efforts to synthesize their structurally unique motifs. In this report, a approach from a readily available lactic acid derivative is devised to construct several amino deoxysugars embedded in natural products, featuring a novel nitroso-ene-type cyclization to introduce a nitrogen atom into the carbon framework. This efficient synthesis provides an unprecedented synthetic route to explore the nitroso-ene cyclization to accumulate intriguing amino deoxysugars.
View Article and Find Full Text PDFRapid access to C2-quaternary 3-methyleneindolines base-mediated post-Ugi Conia-ene cyclization.
Chem Commun (Camb)
March 2023
Center for Novel Target and Therapeutic Intervention, Institute of Life Sciences, Chongqing Medical University, Chongqing 400016, China.
Highly efficient synthesis of diverse 2,2-disubstituted 3-methyleneindoline derivatives through a one-pot base-promoted post-Ugi 5--dig "Conia-ene"-type cyclization has been disclosed. The mechanism study indicates that an intramolecular hydrogen bond may play a vital role in this process. The antiproliferative evaluation of cancer cell lines reveals that this protocol provides practical use in the green synthesis of bioactive compound libraries.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!