Mukaiyama aldolisation reactions of α,β-epoxyaldehydes in aqueous media

Ruland, Yvan; Noereuil, Pierre; Baltas, Michel

doi:10.1016/j.tet.2005.07.027

Cited by 10 publications

(2 citation statements)

References 25 publications

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“…In this case, no general preparative methods are available, and a very limited number of specific preparations includes the synthesis from stable heterocyclic enol derivatives and from α-phosphono-α-silyloxy amides through an olefination reaction . On the contrary, α-silyloxy acrylic esters have been extensively used for the preparation of biomolecules, in radical reactions, or for the synthesis of α,β-unsaturated ketoesters …”

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Photoinduced Multicomponent Synthesis of α-Silyloxy Acrylamides, an Unexplored Class of Silyl Enol Ethers

et al. 2018

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The photoinduced, multicomponent reaction of α-diazoketones, silanols, and isocyanides affords α-silyloxy acrylamides, formally derived from α-keto amides. The presence of a secondary amido group makes classic preparative methods for silyl enol ethers unfeasible in this case, while the mild conditions required by this photochemical approach allow their synthesis in good yields; moreover, the general structure can be easily modified by varying each component of the multicomponent reaction. Fine-tuning of the reaction conditions (i.e., solvents, radiation, additives) can be exploited to obtain complete Z selectivity. The reactivity of this overlooked class of silyl enol ethers has been investigated, and features that could pave the way to new applications have been found.

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Photoinduced Multicomponent Synthesis of α-Silyloxy Acrylamides, an Unexplored Class of Silyl Enol Ethers

et al. 2018

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“…The reactions of cis and trans α,β-epoxy aldehydes with ketene silyl acetals proceeded using the Sc(OTf) 3 -SDS system in water were studied. 78 The use of cosolvents failed to generate the aldol adducts, while the best results were obtained when operating under the micellar system with high anti -diastereofacial preference. The reaction of benzylated epoxy aldehyde 31 with ketene silyl acetal 32 derived from ethyl pyruvate led to ulosonic ester derivatives 33 (Scheme 16 ).…”

Section: The Mukaiyama Aldol Reactions In 100% Watermentioning

confidence: 99%

Mukaiyama Aldol Reactions in Aqueous Media

Kitanosono

Kobayashi

2013

Adv Synth Catal

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Mukaiyama aldol reactions in aqueous media have been surveyed. While the original Mukaiyama aldol reactions entailed stoichiometric use of Lewis acids in organic solvents under strictly anhydrous conditions, Mukaiyama aldol reactions in aqueous media are not only suitable for green sustainable chemistry but are found to produce singular phenomena. These findings led to the discovery of a series of water-compatible Lewis acids such as lanthanide triflates in 1991. Our understanding on these beneficial effects in the presence of water will be deepened through the brilliant examples collected in this review.1 Introduction2 Rate Enhancement by Water in the Mukaiyama Aldol Reaction3 Lewis Acid Catalysis in Aqueous or Organic Solvents3.1 Water-Compatible Lewis Acids4 Lewis-Base Catalysis in Aqueous or Organic Solvents5 The Mukaiyama Aldol Reactions in 100% Water6 Asymmetric Catalysts in Aqueous Media and Water7 Conclusions and Perspective

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Methyl 2-(Trimethylsiloxy)Acrylate

Selig

Bach

2010

Encyclopedia of Reagents for Organic Synthesis

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Mukaiyama aldolisation reactions of α,β-epoxyaldehydes in aqueous media

Cited by 10 publications

References 25 publications

Photoinduced Multicomponent Synthesis of α-Silyloxy Acrylamides, an Unexplored Class of Silyl Enol Ethers

Photoinduced Multicomponent Synthesis of α-Silyloxy Acrylamides, an Unexplored Class of Silyl Enol Ethers

Mukaiyama Aldol Reactions in Aqueous Media

Methyl 2-(Trimethylsiloxy)Acrylate

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