A Lewis acid-mediated, 5/6/7/8- reductive hydroalkoxylation cascade on enynols gives expeditious, diastereoselective access to small and medium ring cyclic ethers with a long aliphatic side chain. The brevity of the approach allowed a 4-step, stereoselective total synthesis of (±)-isolaurepan and (±)--lauthisan.
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Unlocking a reductive hydroalkoxylation cascade for the stereoselective synthesis of cyclic ethers: total synthesis of (±)-isolaurepan and (±)--lauthisan.
Chem Commun (Camb)
October 2024
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India.
A Lewis acid-mediated, 5/6/7/8- reductive hydroalkoxylation cascade on enynols gives expeditious, diastereoselective access to small and medium ring cyclic ethers with a long aliphatic side chain. The brevity of the approach allowed a 4-step, stereoselective total synthesis of (±)-isolaurepan and (±)--lauthisan.
View Article and Find Full Text PDFDeciphering substitution effects on reductive hydroalkoxylation of alkynyl aminols for stereoselective synthesis of morpholines and 1,4-oxazepanes: total synthesis of tridemorph and fenpropimorph.
Org Biomol Chem
July 2024
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai - 400076, India.
Acid catalysed reductive etherification of -propargyl amino alcohols for the stereoselective synthesis of -2,5/2,6-disubstituted morpholines and -2,6/2,7-disubstituted oxazepanes has been developed. Mechanistic studies revealed that terminal alkynols gave morpholines a 6- hydroalkoxylation-isomerization-reduction cascade. Interestingly, an alkyne hydration-cyclization-reduction sequence is found to be involved in the formation of oxazepanes from alkyl substituted internal alkynols.
View Article and Find Full Text PDFLewis-Acid-Catalyzed Reductive Hydroalkoxylation of Propargylic -Hydroxylamines Gives Stereoselective Access to Isoxazolidines.
Org Lett
April 2023
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
Lewis-acid-catalyzed 5 reductive hydroalkoxylation cascade on propargylic -hydroxylamine gave expedient, stereoselective access to isoxazolidine derivatives. The developed method provides a new approach toward the synthesis of isoxazolidine, a biologically privileged scaffold. The synthetic potential of the developed methodology was demonstrated by synthesizing 1,3-aminoalcohol, 4-aminotetrahydropyran, and sedamine natural products.
View Article and Find Full Text PDFVisible-light induced metal-free intramolecular reductive cyclisations of ketones with alkynes and allenes.
Chem Commun (Camb)
February 2023
Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstraße 21, Freiburg im Breisgau 79104, Germany.
A visible-light-induced, intramolecular, reductive cyclisation of ketones with an unsaturated hydrocarbon moiety was developed. In contrast to conventional protocols requiring resource precious or hazardous metal sources, this method enables facile access to ketyl radicals under metal-free and mild reaction conditions. By polarity-reversed, ketyl radical hydroalkoxylation of alkynes and allenes, a variety of five-membered (hetero-)cyclic products were generated in good yields with good to excellent stereoselectivities.
View Article and Find Full Text PDFA Triple Photoredox/Cobalt/Brønsted Acid Catalysis Enabling Markovnikov Hydroalkoxylation of Unactivated Alkenes.
J Am Chem Soc
May 2022
Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan.
Article Synopsis
- This research showcases a method for Markovnikov hydroalkoxylation of unactivated alkenes using alcohols through a triple catalysis involving photoredox, cobalt, and Brønsted acid catalysts under visible light.
- The process involves three main steps: generating Co(III) hydride, facilitating hydrogen atom transfer from the hydride to the alkene, and oxidizing the resulting alkyl Co(III) complex to alkyl Co(IV).
- This innovative approach enables precise control of protons and electrons, eliminating the need for strong acids and other external agents typically required in traditional methods.
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