Reactions that involve metal enolate species are amongst the most versatile carbon-carbon bond forming processes available to synthetic chemists. Enolate species are involved in a multitude of powerful applications in asymmetric organic synthesis, but the generation of fully substituted enolates in a geometrically defined form is not easily achieved especially in acyclic systems. In this Feature Article we focus on the most prominent examples reported in the literature describing the formation of highly diastereo- and enantiomerically enriched quaternary stereocentres in acyclic molecules derived from stereodefined non-cyclic trisubstituted metal enolates.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c4cc04391j | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Chemodivergent, enantio- and regioselective couplings of alkynes, aldehydes and silanes enabled by nickel/N-heterocyclic carbene catalysis.
Sci Bull (Beijing)
December 2024
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China. Electronic address:
Divergent synthesis of valuable molecules through common starting materials and metal catalysis represents a longstanding challenge and a significant research goal. We here describe chemodivergent, highly enantio- and regioselective nickel-catalyzed reductive and dehydrogenative coupling reactions of alkynes, aldehydes, and silanes. A single chiral Ni-based catalyst is leveraged to directly prepare three distinct enantioenriched products (silyl-protected trisubstituted chiral allylic alcohols, oxasilacyclopentenes, and silicon-stereogenic oxasilacyclopentenes) in a single chemical operation.
View Article and Find Full Text PDFPhotoinduced synthesis of trisubstituted allylic molecules migratory allylation of olefins.
Chem Commun (Camb)
January 2025
Shanghai Frontiers Science Center for Chinese Medicine Chemical Biology, Institute of Interdisciplinary Integrative Medicine Research, Shanghai University of Traditional Chinese Medicine, No. 1200, Cailun Road, Shanghai 201203, China.
A transition-metal-free method to afford diverse trisubstituted allylic molecules migratory allylation of olefins under light irradiation is described. This system tolerated diverse -tosylhydrazones and olefinic boronic acids. Successful allylation of drugs and natural-product analogues was achieved.
View Article and Find Full Text PDFLigand Assisted Co(II)-Catalyzed Multicomponent Synthesis of Substituted Pyrroles and Pyridines.
Chem Asian J
December 2024
Indian Institute of Engineering Science and Technology, Chemistry, Botanic Garden, 711103, Howrah, INDIA.
Herein, we describe a sustainable Co(II)-catalyzed synthesis of pyrroles and pyridines. Using a Co(II)-catalyst [CoII2(La)2Cl2] (1a) bearing redox-active 2-(phenyldiazenyl)-1,10-phenanthroline) (La) scaffold, various substituted pyrroles and pyridines were synthesized in good yields, taking alcohol as one of the primary feedstock. Pyrroles were synthesized by the equimolar reaction of 2-amino and secondary alcohols.
View Article and Find Full Text PDFB(CF)-Catalyzed Regiodivergent Thioetherifications of Alkenes via Thiiranium Intermediates: Experimental and Computational Insights.
Chemistry
December 2024
Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Translational Research Hub, Maindy Road, Cathays, Cardiff, Cymru/Wales, CF24 4HQ, UK.
Precise control of selective alkene functionalization is a continuing challenge in the chemical community. In this study, we develop a substitution-controlled regiodivergent thioetherification of di- or trisubstituted alkenes using 10 mol % tris(pentafluorophenyl)borane [B(CF)] as a catalyst and N-thiosuccinimide as a sulfenylating reagent. This metal-free borane catalyzed C-S bond forming method is utilized for a Csp-H sulfenylation reaction to synthesize an array of diphenylvinylsulfide derivatives with good to excellent yields (25 examples, up to 91 % yield).
View Article and Find Full Text PDFRegioselective Synthesis of -Aryl Pyrazoles from Alkenyl Sulfoxonium Ylides and Aryl Diazonium Salts.
J Org Chem
December 2024
Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi 110016, India.
A convenient and practical method has been developed for synthesizing various -aryl pyrazoles from vinyl sulfoxonium ylides and diazonium salts. When using 1,3-disubstituted vinyl sulfoxonium ylides, the reaction selectively yields 1,3,5-trisubstituted pyrazoles. On the other hand, employing 2,3-disubstituted vinyl sulfoxonium ylides results in the formation of 1,3,4-trisubstituted pyrazoles.
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!