A divergent synthesis of both diastereoisomers of (+/-)-(3-aminocyclopentane)alkylphosphinic acid is described. Both diastereoisomers are obtained in 5 steps from the key (+/-)-(3-hydroxycyclopent-1-ene)alkylphosphinate esters which are prepared via a palladium catalysed C-P bond forming reaction.
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J Org Chem
January 2025
Evotec (US) Inc., 303B College Road East, Princeton, New Jersey 08540, United States.
A novel, highly diastereoselective, and metal-free synthesis of multisubstituted piperidines via an S1 approach is reported in this study. The method allows for the preparation of highly functionalized compounds with exceptional diastereomeric selectivities and consistently reproducible yields. These compounds are of significant interest due to their remarkable biological activities toward influenza endonuclease.
View Article and Find Full Text PDFACS Catal
December 2024
Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
A Rh(III)-catalyzed sequential C-H bond addition to dienes and in situ formed aldimines was developed, allowing for the preparation of otherwise challenging to access amines with quaternary centers at the -position. A broad range of dienes were effective inputs and installed a variety of aryl and alkyl substituents at the quaternary carbon site. Aryl and alkyl sulfonamide and carbamate nitrogen substituents were incorporated by using different formaldimine precursors.
View Article and Find Full Text PDFOrg Lett
January 2025
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
TMSOTf-mediated 5/6-- hydroalkoxylation followed by the (3 + 2) cycloaddition cascade reaction of hydroxy cyclopropenes with aldehydes gave an expedient, stereoselective synthesis of [5.5]-and [6.5]-spiroketal derivatives.
View Article and Find Full Text PDFBioorg Chem
December 2024
CSIR- Indian Institute of Integrative Medicine, Canal Road, Jammu 180001, India; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India. Electronic address:
Alantolactone and isoalantolactone are two isomeric sesquiterpene lactones that were isolated from Innula recemosa. Here, we are used for the semisynthesis of novel isoxazolidine hybrids of alantolactone and isoalantolactone through a two-step process: nitrone synthesis followed by nitrone 1,3-dipolar cycloaddition. The formation of the cycloadduct was well characterized via modern spectroscopic techniques such as HRMS, H NMR, C NMR, DEPT-90, DEPT-135, and 2D NMR.
View Article and Find Full Text PDFOrg Lett
December 2024
Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University, Nanning 530001, P. R. China.
A palladium-catalyzed [2π + 2σ] cycloaddition of vinyl bicyclo[1.1.0]butanes with methyleneindolinones has been developed.
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