Journal Article10.1021/ACS.CHEMREV.8B00261
Phosphine-Catalyzed Asymmetric Organic Reactions.
594
TL;DR: This review summarizes all of the literature examples from late 1990s to the end of 2017, alongside their mechanistic insights whenever possible, with a very aim to trigger more intensive research in the future to render asymmetric phosphine catalysis one of the most common and reliable tools to organic chemists.
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Abstract: Asymmetric phosphine catalysis showcasing remarkable progress over the past two decades has emerged as a key synthetic platform for the creation of molecular frameworks encountered in medicinal chemistry and materials science. Different types of novel chiral phosphine catalysts have been developed and employed in cornucopias of organic transformations, such as annulation, addition, Morita–Baylis–Hillman, and Rauhut–Currier reactions, among others. This review summarizes all of the literature examples from late 1990s to the end of 2017, alongside their mechanistic insights whenever possible, with a very aim to trigger more intensive research in the future to render asymmetric phosphine catalysis one of the most common and reliable tools to organic chemists.
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References
Enantioselective [4+2] cycloaddition reaction of α,β-unsaturated imine and methyl vinyl ketone catalyzed by chiral phosphine
TL;DR: This methodology establishes a new protocol for the asymmetric construction of functionalized tetrahydropyridines for the enantioselective [4+2] cycloaddition between α,β-unsaturated imines and methyl vinyl ketone.
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Bifunctional ferrocene-based squaramide-phosphine as an organocatalyst for highly enantioselective intramolecular Morita–Baylis–Hillman reaction
TL;DR: This work demonstrates that, in accord with metal catalysis, ferrocene could be an excellent scaffold for organocatalysts.
30
Access to 2′,3′-dihydro-1′H-spiro[indoline-3,4′-pyridin]-2-ones via amino acid derived phosphine-catalyzed asymmetric [4+2] annulation with easily available oxindole-derived α,β-unsaturated imines
TL;DR: The phosphine-catalyzed asymmetric annulation of vinyl ketones with more easily available oxindole-derived α,β-unsaturated imines has been further developed in the presence of an easily available multifunctional thiourea-phosphine catalyst derived from natural amino acid, providing the enantioselective synthesis of 2′,3′-dihydro-1′H-spiro[indoline-3,4′-pyrid
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Asymmetric Construction of Spirocyclopentenebenzofuranone Core Structures via Highly Selective Phosphine-Catalyzed [3 + 2] Cycloaddition Reactions.
TL;DR: In this paper, a chiral 1,2-ethanediylphospholane as a catalyst was used for cycloaddition with Morita-Baylis-Hillman carbonates.
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Kinetic Resolution of Hydroperoxides with Enantiopure Phosphines: Preparation of Enantioenriched Tertiary Hydroperoxides.
TL;DR: In this paper, an efficient reductive kinetic resolution strategy capable of accessing optically active tertiary hydroperoxides is reported, which can be resolved with commercially available (R)- or (S)-xylyl-PHANEPHOS with selectivity factors as large as 37.