The highly enantioselective catalytic aza-Morita–Baylis–Hillman reaction

Hu, Fangdong; Shi, Min

doi:10.1039/c4qo00026a

Cited by 32 publications

(6 citation statements)

References 74 publications

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“…Similarly, the reaction involving imines is known as the aza-Baylis–Hillman reaction. Phosphine-catalyzed MBH reactions, aza-Morita–Baylis–Hillman reactions, their enantioselective variants, and their applications have been summarized in a vast range of accounts and reviews, − especially some recent reviews, − and, therefore, will not be further discussed herein.…”

Section: Nucleophilic Phosphine Catalysis Of Alkenesmentioning

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: Nucleophilic Phosphine Catalysis Of Alkenesmentioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

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“…The asymmetric aza-Morita-Baylis-Hillman (aza-MBH) is widely recognized as a useful and atom-economical carbon-carbon bond formation reaction between electrondeficient alkenes and imines catalyzed by chiral Lewis bases (selected reviews; [141][142][143][144]). This transformation provides highly functionalized β-amino carbonyl compounds in an enantio-enriched form.…”

Section: Activated And/or Cyclic Ketimines In Aza-morita-baylis-hillman Reactionmentioning

confidence: 99%

Asymmetric Catalytic Ketimine Mannich Reactions and Related Transformations

Reep

Jarvis

et al. 2021

Catalysts

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The catalytic enantioselective ketimine Mannich and its related reactions provide direct access to chiral building blocks bearing an α-tertiary amine stereogenic center, a ubiquitous structural motif in nature. Although ketimines are often viewed as challenging electrophiles, various approaches/strategies to circumvent or overcome the adverse properties of ketimines have been developed for these transformations. This review showcases the selected examples that highlight the benefits and utilities of various ketimines and remaining challenges associated with them in the context of Mannich, allylation, and aza-Morita–Baylis–Hillman reactions as well as their variants.

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“…This is an attractive process, as it is a highly atom economical C–C bond forming reaction and has therefore undergone significant development since these initial reports. Such developments include the incorporation of enantioselectivity, − and an aza variant by substituting the aldehyde/ketone for an imine (Scheme B) . This aza-MBH reaction has been the focus of more recent work, due to the reaction products being desirable β-amino acid derivatives .…”

Section: Introductionmentioning

confidence: 99%

Expedient Organocatalytic Aza-Morita–Baylis–Hillman Reaction through Ball-Milling

Williams

Morrill

Browne

2020

ACS Sustainable Chem. Eng.

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A ball-milling enabled tertiary amine catalyzed aza-Morita–Baylis–Hillman reaction is reported. The reaction process does not require solvent, has significantly shorter reaction times than previous methods and is reported on a range of imines and acrylate Michael acceptors across than 26 examples. A 12-fold scaled-up example is also reported as well as experimental comparisons to solution-based experiments and neat-stirred reactions.

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The highly enantioselective catalytic aza-Morita–Baylis–Hillman reaction

Abstract: Chiral phosphine, amine or metal catalyzed asymmetric aza-MBH reactions of various imines with different Michael acceptors in recent decades have been discussed and the perspectives offered by these new developments have also been demonstrated.

Cited by 32 publications

References 74 publications

Phosphine Organocatalysis

Phosphine Organocatalysis

Asymmetric Catalytic Ketimine Mannich Reactions and Related Transformations

Expedient Organocatalytic Aza-Morita–Baylis–Hillman Reaction through Ball-Milling

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