Asymmetrische Hydrierung von Vinylthioethern: Zugang zu optisch aktiven 1,5‐Benzothiazepinderivaten

Pyrazoleamides are a class of compounds which have received significant attention in the last years in asymmetric catalysis as more reactive and practical surrogates of esters or amides. These readily available reagents have served in a variety of diastereo-and enantioselective metal-and organocatalytic transformations, spanning from simple carbon-carbon or carbon-heteroatom bond formation to cascade and rearrangement reactions, to produce valuable classes of heterocyclic compounds. More recently, pyrazoleamides have proved to be pertinent reagents in asymmetric catalysis merged with photoredox catalysis, and in more challenging stereoselective bond-forming reactions, occurring directly from a visible-light activated substrate/catalyst complex without any charge separation. Both strategies enable new activation concepts useful for the production of difficult-to-access intermediates and pharmaceuticals. In this review, an overview of the progress achieved in asymmetric catalytic reactions of pyrazoleamides from 2015 up to middle 2020, is illustrated. Rearrangements of α-Diazo Pyrazoleamides 7. Combined Metal-and Organocatalysis 8. Pyrazoleamides in Visible-Light-Activated Photochemical Reactions 8.1. Merging Visible Light Photoredox Activation with Asymmetric Catalysis 8.2. Stereocontrolled Direct Photoreactions from Electronically Excited State 8.3. Merging HAT Photocatalysis with Chiral Lewis Acid Catalysis 9.

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Pyrazoleamides in Catalytic Asymmetric Reactions: Recent Advances

Meninno

Franco

Benaglia

et al. 2021

Adv Synth Catal

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Enantioselective Synthesis of Indolines, Benzodihydrothiophenes, and Indanes by C−H Insertion of Donor/Donor Carbenes

et al. 2018

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We employasingle catalyst/oxidant system to enable the asymmetric syntheses of indolines,b enzodihydrothiophenes,a nd indanes by CÀHi nsertion of donor/donor carbenes.T his methodology enables the rapid construction of densely substituted five-membered rings that form the core of many drug targets and natural products.F urthermore,o xidation of hydrazones to the corresponding diazoc ompounds proceeds in situ, enabling ar elatively facile one-or two-pot protocol in which isolation of potentially explosive diazo alkanes is avoided. Regioselectivity studies were performed to determine the impact of sterics and electronics in donor/donor metal carbene C À Hinsertions to form indolines.This methodology was applied to av ariety of substrates in high yield, diastereomeric,and enantiomeric ratios and to the synthesis of ap atented indane estrogen receptor agonist with anti-cancer activity.

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Chemo‐ and Enantioselective Hydrogenation of α‐Formyl Enamides: An Efficient Access to Chiral α‐Amido Aldehydes

et al. 2019

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In order to effectively synthesize chiral a-amino aldehydes,which have awide range of potential applications in organic synthesis and medicinal chemistry,ahighly chemoand enantioselective hydrogenation of a-formyl enamides has been developed, catalyzedb yarhodium complex of aPstereogenic bisphosphine ligand. Under different hydrogen pressures,the chiral a-amido aldehydes and b-amido alcohols were obtained in high yields (97-99 %) and with excellent chemo-and enantioselectivities (up to > 99.9 %ee). The hydrogenation can be carried out on ag ram scale and with ah igh substrate/catalyst ratio (up to 20 000 S/C), and the hydrogenated products were further converted into several important chiral products.Computations of the catalytic cycle gave ac lear description for the R/S pathways, provided ar easonable explanation for the enantioselectivity,a nd revealed several other specific features. Scheme 1. Asymmetric synthesis of chiral aldehydes. Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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Asymmetrische Hydrierung von Vinylthioethern: Zugang zu optisch aktiven 1,5‐Benzothiazepinderivaten

Cited by 15 publications

References 50 publications

Pyrazoleamides in Catalytic Asymmetric Reactions: Recent Advances

Pyrazoleamides in Catalytic Asymmetric Reactions: Recent Advances

Enantioselective Synthesis of Indolines, Benzodihydrothiophenes, and Indanes by C−H Insertion of Donor/Donor Carbenes

Chemo‐ and Enantioselective Hydrogenation of α‐Formyl Enamides: An Efficient Access to Chiral α‐Amido Aldehydes

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