Catalytic Enantioselective Cycloaddition with Chiral Lewis Bases

Lalli, Claudia; Brioche, Julien; Bernadat, Guillaume; Masson, Géraldine

doi:10.2174/138527211798109178

Cited by 11 publications

(2 citation statements)

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“…Once considered a novelty, nucleophilic phosphine catalysis today provides reliable means to prepare synthetic intermediates and products in all areas of Organic Chemistry, including medicinal agents, natural products, ligands for catalysis, and materials. − While reports of asymmetric variants and the applications of known phosphine-catalyzed reactions grow, the majority of research efforts of late have been dedicated to the development of “new” reactions. To aid active practitioners, as well as the general synthetic chemistry audience, in their understanding of this fast-growing area of research, this Review first categorizes the modes of nucleophilic phosphine catalysis based on the carbon–carbon multiple bond-containing starting materials, namely alkenes (section 2), allenes (section 3), alkynes (section 4), and MBH-alcohol derivatives (MBHADs; section 5).…”

Section: Introductionmentioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

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The hallmark of nucleophilic phosphine catalysis is the initial nucleophilic addition of a phosphine to an electrophilic starting material, producing a reactive zwitterionic intermediate, generally under mild conditions. In this Review, we classify nucleophilic phosphine catalysis reactions in terms of their electrophilic components. In the majority of cases, these electrophiles possess carbon–carbon multiple bonds: alkenes (section 2), allenes (section 3), alkynes (section 4), and Morita–Baylis–Hillman (MBH) alcohol derivatives (MBHADs; section 5). Within each of these sections, the reactions are compiled based on the nature of the second starting material—nucleophiles, dinucleophiles, electrophiles, and electrophile–nucleophiles. Nucleophilic phosphine catalysis reactions that occur via the initial addition to starting materials that do not possess carbon–carbon multiple bonds are collated in section 6. Although not catalytic in the phosphine, the formation of ylides through the nucleophilic addition of phosphines to carbon–carbon multiple bond–containing compounds is intimately related to the catalysis and is discussed in section 7. Finally, section 8 compiles miscellaneous topics, including annulations of the Hüisgen zwitterion, phosphine-mediated reductions, iminophosphorane organocatalysis, and catalytic variants of classical phosphine oxide–generating reactions.

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Section: Introductionmentioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

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“…While several highly enantioselective transition-metal-catalyzed (TMC) cycloadditions have been developed in the last decades, it is quite remarkable that most examples so far reported involve intermolecular processes, typically leading to monocyclic products . Progress on intramolecular annulations, which are more interesting from a constructive perspective, has clearly lagged behind . Indeed, enantioselective TMC intramolecular cycloadditions to give seven-membered carbocycles are limited to a handful of [5C + 2C] and [4C + 3C] processes, whereas intramolecular [3C + 2C] annulations toward enantiorich cyclopentane cores are essentially unknown …”

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confidence: 99%