Supporting Information Sunlight-driven Synthesis of -Diketones via Oxidative Coupling of Enamines with Silyl Enol Ethers Catalyzed by [Ru(bpy) 3] 2+ ... Other enamines were prepared according to the literature procedures.2 Silyl enol ether 2a was purchased from TCI. B Watsona and Douglas Hayesb aDepartment of Pure and Applied Chemistry, WESTChem, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, Scotland, UK GlaxoSmithKline, Medicines Research Centre, Gunnels b Wood Road, Stevenage, Hertfordshire, SG1 2NY, UK.
The Mukaiyama aldol addition is an organic reaction and a type of aldol reaction between a silyl enol ether and an aldehyde or formate. The wanted silyl enol ether 22 was obtained in 93 % yield as 1 : 1 mixture of the diastereoisomers containing only 4 % of the unwanted silyl enol ether 21 as side product. Enol silyl ethers and their analogs are one of the most versatile substrate classes and enjoy widespread applications in organic synthesis (Fig.
The protocol provides access to functionalized pyrroles, 1,6‐ketonitriles, pyrrolines and imidazolines via carbon‐centered radicals generated from an initially formed iminyl radical. Enol silyl ethers can be cleaved with nucleophiles such as MeLi, LiNH 2 or R 4 N + F-to give reactive enolates.
Trialkylsilyl enol ethers are versatile intermediates often used as enolate surrogates for the synthesis of carbonyl compounds. An iron‐catalyzed coupling reaction of O ‐acyloximes and O ‐benzoyl amidoximes with silyl enol ethers is reported. Cross-Coupling Reactions Based on Acetals, Mukaiyama, T.; Murakami , M ... Cyclization Reactions of 1,3-Bis-Silyl Enol Ethers and Related Masked Dianions, Langer, P. Synthesis 2002, 441-59.
Yet there are no reports of broadly applicable, catalytic methods for the synthesis of chiral silyl enol ethers carrying latent functionalities useful for synthetic operations beyond the many possible reactions of the silyl enol ether moiety itself. The reaction was discovered by Teruaki Mukaiyama (1927–2018) in 1973. Examples of Kumada, Stille and Suzuki coupling reactions are illustrated. Silyl enol ethers are common reagents in organic synthesis as illustrated by the Mukaiyama aldol reaction: Vinyl acetate is an enol ester that is made on an industrial scale. Silyl Enol Ethers. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. Sakurai 177 has found that dicobalt octacarbonyl is an excellent catalyst for the reaction (equation 67) and that the side reactions occurring through the use of the catalysts mentioned above (e.g. Electrooxidative Coupling of Aromatics and Silyl Enol Ethers: Application to the Synthesis of Annulated Aromatics Jeffrey B. Sperry* Mand Dennis L. Wright Dartmouth College Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755 The preparation of annulated furan and benzene systems from a two-step conjugate addition, electrochemical annulation sequence has been … The use of silyl enol ethers as an enolate equivalent in Lewis acid-catalyzed aldol additions. Rl R'^MgX [Ni] R^ 3 <"^R4 Z ' R2-' \ /-- c^=c R2^ ^OSiMes ,c, ^ 1b: Ie: : [_yosiMe3, Ph' 'OSiMea ^s^ CT-lg: \^/^/OSiMe3, (Z)-1g: ^-^__^.OSiMe3.
An iron-catalyzed coupling reaction of O-acyloxime/O-benzoyl amidoximes with silyl enol ethers is reported. As a starting point of our work, iodide 1a and silyl enol ether 2a, both originating from acetophenone, were selected as model substrates, and their coupling was evaluated . The silyl enol ether 22 could be stored for months at - 20 °C in the refrigerator. A particular intriguing example involves a one‐pot synthesis of silyl enol ether 1j by means of a Diels−Alder reaction, subsequent nonaflation and a Heck reaction with tert‐butyl acrylate, furnishing the highly functionalised 1,3‐diene 30 in good overall yield.
3. The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine.This can be compared with enol, which is a functional group containing both alkene (en-) and alcohol (-ol).Enamines are considered to be nitrogen analogs of enols. The anionic charge is delocalized over the oxygen and the two carbon sites. [19,24] These enol silanes are desireable enolate precursors since in many cases they are significantly easier to prepare than the corresponding allyl enol carbonates. (© … If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. the efficient preparation of silyl enol ethers’ William J. Kerr,*a Allan J. We examined silyl glyoximides, a new class of reagents recently synthesized by Hsung and co-workers in conjunction with ynamide oxidation studies.
Other silyl enol …
silyl ether formation) may be avoided. Supporting Information 1. The trimethylsilyl group is thought of as a sterically demanding hydrogen equivalent that activates the enol and traps the aldol hydroxyl. Synthesis of silyl enol ethers and related compounds. The silyl enolates can be readily converted into novel enantiopure vinyl triflates, a class of highly versatile cross-coupling reagents, enabling the syntheses of other enantiomerically pure, stereo-defined trisubstituted alkene intermediates not easily accessible by current methods. Recent Literature.
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