Stereoselective Synthesis of 4‐Hydroxy‐1‐Silyl‐1‐Allenylboranes and Access to 2‐Silylethynyl‐1,3‐Diols
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DOI: 10.1002/ajoc.202400042
Abstract: The highly stereoselective gem‐silylboration of chiral 2‐substituted 1‐ethynylepoxides is reported herein. The reaction involves first the deprotonation of the epoxides in the acetylenic position followed by transmetallation with Et3SiBpin. The transient silylborane ate‐complexes generated undergo… read more here.
Keywords: allenylboranes access; synthesis hydroxy; silyl allenylboranes; hydroxy silyl ... See more keywords
Metal‐free stereoselective synthesis of tetrahydropyrans bearing adjacent quaternary and tertiary stereocenters by acid mediated cyclization
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DOI: 10.1002/ajoc.202400096
Abstract: A convenient route for the preparation of tetrahydropyran (THP) derivatives with a quaternary and tertiary vicinal stereocenters is reported. The atom economy acid‐catalyzed cyclization of allylsilyl alcohols provided polysubstituted tetrahydropyrans in good yields and excellent… read more here.
Keywords: quaternary tertiary; metal free; cyclization; stereoselective synthesis ... See more keywords
Ir‐Catalyzed Sulfur‐Directed Vinylic C─H Activation for the Stereoselective Synthesis of 1,3‐Dienes Using Alkynoates
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DOI: 10.1002/ajoc.202500192
Abstract: Vinylic sp2 C─H alkenylation with alkynoates was investigated in the presence of a cationic iridium catalyst using aryl 2‐substituted allyl sulfides as substrates. In the reaction of dimethyl acetylenedicarboxylate, the double bonds were isomerized from… read more here.
Keywords: sulfur directed; vinylic activation; activation stereoselective; directed vinylic ... See more keywords
Highly Stereoselective Synthesis of Imidazolidines through the Palladium(0)‐Catalyzed Three‐Component Reaction of 2,3‐Allenylamines, Organic Halides, and Imines
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DOI: 10.1002/cctc.201601345
Abstract: A new and efficient method for the synthesis of polysubstituted imidazolidines through the Pd0‐catalyzed double addition/cyclization of 2,3‐allenylamines with aryl iodides and imines was explored. This catalytic reaction afforded the desired products in good yields… read more here.
Keywords: highly stereoselective; imidazolidines palladium; stereoselective synthesis; synthesis imidazolidines ... See more keywords
Stereoselective synthesis of 3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one derivatives as PIM kinase inhibitors inspired from marine alkaloids.
Sign Up to like & getrecommendations! Published in 2022 at "Chirality"
DOI: 10.1002/chir.23501
Abstract: We previously demonstrated that natural product-inspired 3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-ones derivatives delivered potent and selective PIM kinases inhibitors however with non-optimal ADME/PK properties and modest oral bioavailability. Herein, we describe a structure-based scaffold decoration and a stereoselective approach… read more here.
Keywords: synthesis dihydropyrrolo; dihydropyrrolo pyrazin; pyrazin one; synthesis ... See more keywords
Stereoselective Synthesis of Tetrahydroisoquinolines from Chiral 4-Azaocta-1,7-diynes and 4-Azaocta-1,7-enynes
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DOI: 10.1002/ejoc.201901590
Abstract: We thank the continued financial support from the Ministerio de Economia y Competitividad (MINECO; project CTQ2014-53695-P, CTQ2014-51912-REDC, CTQ2016-81797-REDC, CTQ2017-85093-P), Ministerio de Ciencia, Innovacion y Universidades (RED2018-102387-T), FEDER, the Generalitat Valenciana (PROMETEOII/2014/017), ant the University of… read more here.
Keywords: chiral azaocta; diynes azaocta; stereoselective synthesis; synthesis tetrahydroisoquinolines ... See more keywords
Blue‐Light‐Induced Stereoselective Synthesis of α‐Alkylated Amino Acid Derivatives
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DOI: 10.1002/ejoc.202401477
Abstract: A photoredox‐catalyzed decarboxylative C(sp3)−H alkylation of glycine derivatives, utilizing (+)/(−)‐camphorsultam as a chiral auxiliary and alkyl N‐hydroxyphthalimide (NHP) ester as a radical precursor, has been developed, providing an efficient approach for the stereoselective synthesis of… read more here.
Keywords: amino acid; blue light; stereoselective synthesis; acid derivatives ... See more keywords
Diazo compounds under visible light: Stereoselective synthesis of cyclic architectures
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DOI: 10.1002/ejoc.202500329
Abstract: Diazo compounds are versatile and valuable reagents in organic synthesis. The reaction of diazo substrates under photochemical conditions find high selectivity compared to that under thermal conditions. In the presence of light, they can act… read more here.
Keywords: stereoselective synthesis; visible light; diazo compounds; synthesis cyclic ... See more keywords
Stereoselective Synthesis of Unsymmetrical 3,3‐Diarylpropenals by a Suzuki‐Miyaura Reaction of (Z)‐3‐Aryl‐3‐chloropropenal Intermediates
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DOI: 10.1002/ejoc.202500497
Abstract: Using (Z)‐3‐aryl‐3‐chloropropenals, we have developed an efficient route for the stereoselective synthesis of unsymmetrical 3,3‐diarylpropenals in high yield with very good retention of stereochemistry. Consequently, we have found an efficient route for the stereoselective synthesis… read more here.
Keywords: synthesis unsymmetrical; suzuki miyaura; stereochemistry; unsymmetrical diarylpropenals ... See more keywords
Highly Stereoselective Synthesis of New Aziridines via Baldwin Rearrangement and Their Potential Biological Activities
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DOI: 10.1002/jhet.2548
Abstract: An atom-economical conversion of N-substituted isoxazoline derivatives to new N-substituted aziridines has been described using microwave irradiation through Baldwin rearrangement. N-substituted isoxazoline derivatives have been synthesized using a variety of nitrones and alkynes via 1,3-dipolar… read more here.
Keywords: highly stereoselective; synthesis new; stereoselective synthesis; baldwin rearrangement ... See more keywords
Stereoselective Synthesis of Pear Ester
Sign Up to like & getrecommendations! Published in 2017 at "Chemistry of Natural Compounds"
DOI: 10.1007/s10600-017-2191-0
Abstract: A simple two-step synthesis of ethyl-(2E,4Z)-deca-2,4-dienoate based on Fe-catalyzed cross-coupling of ethyl-(2E,4Z)-5-chloropenta-2,4-dienoate, which was obtained via one-pot oxidation and olefination of readily available (2Z)-3-chloroprop-2-en-1-ol by n-pentylmagnesiumbromide, was developed. read more here.
Keywords: synthesis pear; stereoselective synthesis; chemistry; pear ester ... See more keywords