Preparation of α-Imino Aldehydes by [1,3]-Rearrangements of <i>O</i>-Alkenyl Oximes

Kontokosta, Dimitra; Mueller, Daniel S.; Wang, Heng Yen; Anderson, Laura L.

doi:10.1021/ol402237w

Cited by 23 publications

(4 citation statements)

References 46 publications

(18 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Benzophenone oxime 61 reacted with a 4-fold excess of AlkCHCHB(OH) 2 (67) in the presence of copper(I) t h i o p h e n e -2 -c a r b o x y l a t e ( C u T C ; 1 e q u i v ) , 1, 4diazabicyclo[2.2.2]octane (DABCO; 3-fold excess), AgClO 4 (0.5 equiv), and Na 2 SO 4 in 1,2-dichloroethane at 25 °C for 3 h in air to yield the O-vinyl benzophenone oximes Ph 2 C NOCHCHAlk (68; 56−96%; Scheme 32). 197 When a 2-fold excess of 67 was used, the reaction yields decreased by 26−48%. The copper center activates the B−C bond, and therefore, a reaction route would be similar to the one postulated for the arylation involving ArB(OH) 2 (Section 3.1.2).…”

Section: Chemical Reviewsmentioning

confidence: 99%

Metal-Involving Synthesis and Reactions of Oximes

et al. 2017

View full text Add to dashboard Cite

This review classifies and summarizes the past 10-15 years of advancements in the field of metal-involving (i.e., metal-mediated and metal-catalyzed) reactions of oximes. These reactions are diverse in nature and have been employed for syntheses of oxime-based metal complexes and cage-compounds, oxime functionalizations, and the preparation of new classes of organic species, in particular, a wide variety of heterocyclic systems spanning small 3-membered ring systems to macroheterocycles. This consideration gives a general outlook of reaction routes, mechanisms, and driving forces and underlines the potential of metal-involving conversions of oxime species for application in various fields of chemistry and draws attention to the emerging putative targets.

show abstract

Section: Chemical Reviewsmentioning

confidence: 99%

Metal-Involving Synthesis and Reactions of Oximes

et al. 2017

View full text Add to dashboard Cite

show abstract

“…In 2013, Anderson and co-workers reported the Cu-mediated thermal [1,3]-rearrangement of benzophenone Oalk-1-enyloximes to give -imino aldehydes. 92 The benzophenone O-alk-1-enyloximes were synthesized by C-O bond coupling between alk-1-enylboronic acids and benzophenone oximes (Scheme 112). The -imino aldehydes were used in the Horner-Wadsworth-Emmons olefination to give -imino-,-unsaturated esters.…”

Section: Review Synthesis Scheme 111 Mechanistic Overview Of Enol Acementioning

confidence: 99%

Advances in Carbon–Element Bond Construction under Chan–Lam Cross-Coupling Conditions: A Second Decade

et al. 2020

View full text Add to dashboard Cite

Copper-mediated carbon–heteroatom bond-forming reactions involving a wide range of substrates have been in the spotlight for many organic chemists. This review highlights developments between 2010 and 2019 in both stoichiometric and catalytic copper-mediated reactions, and also examples of nickel-mediated reactions, under modified Chan–Lam cross-coupling conditions using various nucleophiles; examples include chemo- and regioselective N-arylations or O-arylations. The utilization of various nucleophiles as coupling partners together with reaction optimization (including the choice of copper source, ligands, base, and other additives), limitations, scope, and mechanisms are examined; these have benefitted the development of efficient and milder methods. The synthesis of medicinally valuable or pharmaceutically important nitrogen heterocycles, including isotope-labeled compounds, is also included. Chan–Lam coupling reaction can now form twelve different C–element bonds, making it one of the most diverse and mild reactions known in organic chemistry.1 Introduction2 Construction of C–N and C–O Bonds2.1 C–N Bond Formation2.1.1 Original Discovery via Stoichiometric Copper-Mediated C–N Bond Formation2.1.2 Copper-Catalyzed C–N Bond Formation2.1.3 Coupling with Azides, Sulfoximines, and Sulfonediimines as Nitrogen Nucleophiles2.1.4 Coupling with N,N-Dialkylhydroxylamines2.1.5 Enolate Coupling with sp3-Carbon Nucleophiles2.1.6 Nickel-Catalyzed Chan–Lam Coupling2.1.7 Coupling with Amino Acids2.1.8 Coupling with Alkylboron Reagents2.1.9 Coupling with Electron-Deficient Heteroarylamines2.1.10 Selective C–N Bond Formation for the Synthesis of Heterocycle-Containing Compounds2.1.11 Using Sulfonato-imino Copper(II) Complexes2.2 C–O Bond Formation2.2.1 Coupling with (Hetero)arylboron Reagents2.2.2 Coupling with Alkyl- and Alkenylboron Reagents3 C–Element (Element = S, P, C, F, Cl, Br, I, Se, Te, At) Bond Forma tion under Modified Chan–Lam Conditions4 Conclusions

show abstract

“…In the same year, Anderson and co-workers also reported a method to synthesize O-vinyl oximes through a copper thiophenecarboxylate (CuTC)-mediated cross-coupling of benzophenone oxime with trans-vinylboronic acids (Scheme 36). 34 Various trans-vinyl boronic acids were evaluated in this construction of O-vinyl oximes. Linear and branched alkyl substituents on the vinylboronic acids gave the corresponding products smoothly.…”

Section: Review Syn Thesis Scheme 34 Diastereoselective Rearrangementmentioning

confidence: 99%