Chiral phosphinothiourea organocatalyst in the enantioselective Morita–Baylis–Hillman reactions of aromatic aldehydes with methyl vinyl ketone

Yuan, Kui; Zhang, Lei; Song, Hantao; Hu, Yinjun; Wu, Xin‐Yan

doi:10.1016/j.tetlet.2008.08.042

Cited by 79 publications

(26 citation statements)

References 24 publications

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“…We first carried out the reaction with MVK, p ‐QM 1 a , and phosphine‐thiourea 3 a (10 mol %) in CH 2 Cl 2 at 25 °C to test the feasibility of the RC‐type 1,6‐conjugate addition. The desired 1,6‐conjugate addition product was obtained in 87 % yield with 32 % ee (Table , entry 1).…”

Section: Methodsmentioning

confidence: 99%

Enantioselective Rauhut–Currier‐Type 1,6‐Conjugate Addition of Methyl Vinyl Ketone to para‐Quinone Methides

Kang

et al. 2017

Chemistry A European J

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Section: Methodsmentioning

confidence: 99%

Enantioselective Rauhut–Currier‐Type 1,6‐Conjugate Addition of Methyl Vinyl Ketone to para‐Quinone Methides

Kang

et al. 2017

Chemistry A European J

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“…Given the popularity of amine‐thiourea catalysts, Wu et al. reported the synthesis of thiourea based phosphine catalyst ( BFP‐5 ) . Within 15 minutes the MBH adduct could be isolated in 75 % yield and 94 % ee for the reaction between 4‐nitrobenzaldehyde and MVK.…”

Section: Asymmetric Bifunctional Organocatalysis Of the Mbh Reactionmentioning

confidence: 99%

Cooperative Trifunctional Organocatalysts for Proficient Proton Transfer Reactions

Kenny

Liu

2016

Chem. Rec.

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Cooperativity is essential to proficient catalysis, and designing biomimetic, cooperative catalysis is a major avenue to finding new and efficient chemical reactions with practical applications. One challenge in designed cooperative catalysis is to access high catalytic proficiency (large enhancement in both rate and enantioselectivity) as seen in biocatalysis. Here described is an approach of developing and investigating trifunctional organocatalysts with three distinct catalytic functionalities, in order to understand how cooperativity could be organized for enantioselective activation that confers the observed proficiency in a tandem Michael-aldol-proton transfer elimination model reaction. This in future may assist in finding not just cooperative but also regulated catalysis to expand the level of catalytic complexity and efficiency in biomimetic systems.

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“…It intrigued us whether one can employ or envision other chiral structure combined with Lewis base and Brønsted acid functions to design novel efficient catalysts for the MBH/aza-MBH reaction. A recent interesting example demonstrated by Wu's group was the cyclohexane-based chiral (thio)urea-phosphine which also achieved the high enantioselectivity in MBH reaction (Scheme 29) [70].…”

Section: Scheme 26mentioning

confidence: 99%

Privileged chiral catalysts in asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reaction

Wei

Shi

2010

Chin. Sci. Bull.

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In the past decade, the asymmetric Morita-Baylis-Hillman (MBH)/aza-Morita-Baylis-Hillman (aza-MBH) reaction has attracted great attention because it leads to the formation of densely functionalized products in a catalytic and atom-economic way. The MBH/aza-MBH adducts can be further applied in a wide variety of organic synthesis, such as peptide synthesis and heterocyclic compounds synthesis. After a lot of attempts to improve the enantioselectivity, many types of chiral organocatalysts have been identified as highly enantioselective organocatalysts in MBH/aza-MBH reaction. Especially, certain "privileged chiral catalysts" are highly enantioselective in MBH/aza-MBH reaction, which are designed and developed through introducing bi-/multi-functional groups on the so-called "privileged structures" such as cinchona alkaloids, BINAP/BINOL. This review summarizes the exciting advances about the design and development of chiral catalysts derived from "privileged structures" and their applications in asymmetric MBH/aza-MBH reaction. Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reaction, privileged chiral catalysts, organocatalysts, chiral amines, chiral phosphines Citation:Wei Y, Shi M. Privileged chiral catalysts in asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reaction.

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Chiral phosphinothiourea organocatalyst in the enantioselective Morita–Baylis–Hillman reactions of aromatic aldehydes with methyl vinyl ketone

Cited by 79 publications

References 24 publications

Enantioselective Rauhut–Currier‐Type 1,6‐Conjugate Addition of Methyl Vinyl Ketone to para‐Quinone Methides

Enantioselective Rauhut–Currier‐Type 1,6‐Conjugate Addition of Methyl Vinyl Ketone to para‐Quinone Methides

Cooperative Trifunctional Organocatalysts for Proficient Proton Transfer Reactions

Privileged chiral catalysts in asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reaction

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