Journal ArticleDOI
A Fast Catalytic Asymmetric Aza‐Morita–Baylis–Hillman Reaction of N‐Sulfonated Imines with Methyl Vinyl Ketone in the Presence of Chiral Bifunctional Phosphane Lewis Bases
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TLDR
In this article, a series of bifunctional chiral chiral phosphane Lewis bases having one phenyl group and an electron-donating alkyl group on the phosphorus atom was designed and successfully synthesized.About:
This article is published in European Journal of Organic Chemistry.The article was published on 2008-08-01. It has received 32 citations till now. The article focuses on the topics: Lewis acids and bases & Methyl vinyl ketone.read more
Citations
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Catalytic Enantioselective Formation of C−C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update
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Recent contributions from the Baylis-Hillman reaction to organic chemistry.
TL;DR: Acyclic activated alkenes/ alkynes and Asymmetric Baylis-Hillman Reaction: Earlier Developments 5495.
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aza-Baylis−Hillman Reaction
TL;DR: 1.5.1.
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Multifunctional Chiral Phosphine Organocatalysts in Catalytic Asymmetric Morita−Baylis−Hillman and Related Reactions
TL;DR: The refinement of catalysts for the Morita-Baylis-Hillman reaction is described, highlighting a series of multifunctional chiral phosphines that have been developed and synthesized over the past decade, and it is demonstrated that the reactivities and enantioselectivies of these multifunctionals can be adjusted by enhancing the reactive center's nucleophilicity, which can be finely tuned by varying nearby hydrogen-bonding donors.
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Chiral Bifunctional Thiourea–Phosphane Organocatalysts in Asymmetric Allylic Amination of Morita–Baylis–Hillman Acetates
Hong-Ping Deng,Yin Wei,Min Shi +2 more
TL;DR: In this paper, a series of chiral bifunctional thiourea-phosphane catalysts were synthesized and successfully applied in the catalytic, asymmetric allylic amination of MBH (Morita-Baylis-Hillman) acetates derived from the methyl vinyl ketone (MVK), with phthalimide, affording the amination products in up to over 99 % yield and 90 % ee.
References
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Recent Advances in the Baylis−Hillman Reaction and Applications
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The baylis-hillman reaction : a novel carbon-carbon bond forming reaction
TL;DR: In this paper, an approach to chiral Baylis-hillman adducts is presented. But it does not address the problem of chiral activation and self-dimerization of alkenes.
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Synthetic potential of the tertiary-amine-catalysed reaction of activated vinyl carbanions with aldehydes
TL;DR: In this paper, the diaza-1,4bicyclo [2.2] octane, la quinuclidine and ses derives, the quinine
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The Baylis–Hillman reaction: a novel source of attraction, opportunities, and challenges in synthetic chemistry
TL;DR: The Baylis-Hillman reaction is a successful, useful, and atom-economical carbon-carbon bond forming reaction, which has grown from an obscure level to the level of high synthetic popularity due to its operational simplicity and also due to the enormous applications of the Baylis/Hillman adducts in organic synthesis.
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The Enantioselective Morita–Baylis–Hillman Reaction and Its Aza Counterpart
TL;DR: This Minireview summarizes recent mechanistic insights and advances in the design and synthesis of small organic molecules for enantioselective MBH and aza-MBH reactions.