Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
Herein we report a diastereoselective synthesis of boryl-substituted vinylcyclopropanes, a class of highly valuable synthetic building blocks, via deborylative cyclization of geminal diboron compounds. The method exhibits broad functional group tolerance and accommodates diverse alkyl and aryl α-substituents. The diastereoselectivity is primarily governed by the α-substituent (alkyl vs aryl), while olefin geometry in the side chain has a secondary influence. Mechanistic studies indicated distinct pathways: a concerted process for alkyl substrates and a carbanion intermediate for aryl derivatives. Synthetic utility of the products was also demonstrated.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.5c00886 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Preparation of a furfural-derived enantioenriched vinyloxazoline building block and exploring its reactivity.
Beilstein J Org Chem
August 2025
Latvian Institute of Organic Synthesis Aizkraukles 21, Riga, LV-1006, Latvia.
Alloc-protected furfuryl amino alcohols derived from furfural and ʟ- or ᴅ-valinol were subjected to Torii-type ester electrosynthesis to obtain the corresponding unsaturated esters. These served as key intermediates to prepare ()- and enantioenriched unsaturated amides by -Alloc deprotection which induced concomitant methoxymethyl group cleavage, to- rearrangement, and isomerization of the double bond. An oxazoline ring formation in the resulting unsaturated amides provided the corresponding enantioenriched vinyloxazoline.
View Article and Find Full Text PDFRongalite-promoted self-dimerization of 3-acylidene-2-oxindoles: a diastereoselective route to synthesis of bispirooxindoles.
Org Biomol Chem
September 2025
Chemical Engineering and Process Development Division, CSIR-National Chemical Laboratory, Pune-410008, India.
A facile and efficient one-pot rongalite-mediated self-dimerization of 3-acylidene-2-oxindoles has been developed for the diastereoselective synthesis of highly functionalized dispirocyclopentanebisoxindoles. The reaction proceeds a domino sequence involving intermolecular Michael addition followed by intramolecular aldol cyclization under basic conditions. Rongalite, an inexpensive and readily available reagent (∼$0.
View Article and Find Full Text PDFRhodium(II) catalysed highly diastereoselective synthesis of indolyl-pyrrolo[2,1-]isoindoles from phthalimide-derived -sulfonyl-1,2,3-triazoles and indoles.
Org Biomol Chem
September 2025
Department of Chemistry, Indian Institute of Technology, Madras, Tamil Nadu, 600036, India.
A synthetic method has been developed for the diastereoselective domino synthesis of indolyl-pyrrolo[2,1-]isoindoles from phthalimide-derived -sulfonyl-1,2,3-triazoles and indoles. The reaction proceeds ring chain isomerization of triazoles to give α-imino diazo compounds. Then, denitrogenative generation of α-imino Rh(II) carbenes followed by intramolecular oxygen insertion and nucleophilic addition of indoles delivers the indolyl-pyrrolo[2,1-]isoindoles.
View Article and Find Full Text PDFGlycosyl Radical-Based, 1,2-trans-Selective Synthesis of C-Aryl Glycosides from Glycals Enabled by Photoredox PCET/Nickel-Dual Catalysis.
Chemistry
September 2025
National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang, 330022, China.
We report a glycosyl radical-based, 1,2-trans-selective synthesis of C-aryl glycosides of 2-deoxy-2-amino-sugars from glycals via photoredox PCET/Ni dual catalysis. Mechanistic studies indicate that glycosyl radical formation involves the generation of an N-radical through a proton-coupled electron transfer (PCET) process, followed by its addition to the glycal. This protocol features: a) the use of an inexpensive organic photosensitizer and readily available glycals and aryl bromides; b) good functional group tolerance for both aryl bromides and glycal substrates; c) excellent diastereoselectivity, with exclusive formation of the 1,2-trans C-glycosides in all cases.
View Article and Find Full Text PDFStereoselective Synthesis of α-Aminophosphonates and Their Derivatives via Asymmetric α-Azidation of the CAMDOL-Derived Phosphonates.
Org Lett
September 2025
State Key Laboratory of Chemistry for NBC Hazards Protection, Beijing 102205, China.
Optically active α-aminophosphonic acids are unique analogues of α-amino acids, and numerous synthetic methods have been developed. Herein, we present a highly diastereoselective α-azidation approach to the CAMDOL-derived phosphonates, enabling ready access to 27 diverse α-azidophosphonates with defined chirality in up to 85% yield and more than 99:1 dr. Late-stage transformations through the Staudinger reaction or click reaction efficiently delivered the related pharmacological α-aminophosphonic acids or the unique α-triazolylphosphonate derivative, respectively.
View Article and Find Full Text PDF