Imines and related compounds

Intramolecular addition of trialkylboranes to imines and related compounds have been reported and the main results are part of review articles [94, 95]. Addition of ethyl radicals generated from Et3B to aldimines affords the desired addition product in fair to good yield but low diaster control (Scheme 40, Eq. 40a) [96]. Similar reactions with aldoxime ethers [97], aldehyde hydrazones [97], and N-sulfonylaldimines [98] are reported. Radical addition to ketimines has been recently reported (Eq. 40b) [99]. Addition of triethylborane to 2H-azirine-3-carboxylate derivatives is reported [100]. Very recently, Somfai has extended this reaction to the addition of different alkyl radicals generated from trialkylboranes to a chiral ester of 2ff-azirine-3-carboxylate under Lewis acid activation with CuCl (Eq. 40c) [101]. [Pg.103]

Radical addition of organoboranes to imines and related compounds is a promising alternative to the use of classical organometallic compound (see... [Pg.107]

Arene(tricarbonyl)chromium complexes, 19 Nickel boride, 197 to trans-alkenes Chromium(II) sulfate, 84 of anhydrides to lactones Tetrachlorotris[bis(l,4-diphenyl-phosphine)butane]diruthenium, 288 of aromatic rings Palladium catalysts, 230 Raney nickel, 265 Sodium borohydride-1,3-Dicyano-benzene, 279 of aryl halides to arenes Palladium on carbon, 230 of benzyl ethers to alcohols Palladium catalysts, 230 of carboxylic acids to aldehydes Vilsmeier reagent, 341 of epoxides to alcohols Samarium(II) iodide, 270 Sodium hydride-Sodium /-amyloxide-Nickel(II) chloride, 281 Sodium hydride-Sodium /-amyloxide-Zinc chloride, 281 of esters to alcohols Sodium borohydride, 278 of imines and related compounds Arene(tricarbonyl)chromium complexes, 19... [Pg.372]

Imines and related compounds containing a carbon-nitrogen double bond C=N (hydrazones, acylhydrazones, oximes) present the very attractive feature of being double dynamic entities capable of undergoing both ... [Pg.21]

The nucleophilic addition reactions of enolates to imines and related compounds (the so-called Mannich-type reactions, equation 39) are important tools in organic synthesis and a variety of electrophiles have been used to obtain the resulting nitrogen-containing... [Pg.48]

This chapter concerns the net conversion of a C =X ir-bond (X = O and N) to various three-membered ring heterocycles. The most common such process is the conversion of an aldehyde or ketone to a homologous epoxide. These reactions will be discussed along with the analogous process which takes place on imines and related compounds. Additionally, methods to effect the addition of elements other than carbon across either unsaturated system will considered. The synthesis of thiiranes by the addition of carbon across the C—S rr-bond is the subject of a recent comprehensive review and will not be covered here. [Pg.819]

Scheme 2.133 Trifluoromethylation of nitrogen electrophiles, imines, and related compounds (TMS = trimethylsilyl) [80-84].

N. H. Cromwell and M. A. Graff, /. Org. Chem., 17, 414 (1952). Three-Ring Carbonyl Hyperconjugation in Cis and Trans Aryl-Aroyl Ethylene Imines and Related Compounds. [Pg.312]

It has been shown that lanthanide triflates are excellent catalysts for the catalytic activation of imine and related compounds, while most Lewis acids are decomposed or deactivated in the presence of basic nitrogen atoms. For example, (a) Kobayashi S, Bu-sujima T, Nagayama S (1998) J Chem Soc, Chem Commun 19 (b) Kobayashi S, Nagayama S (1997) J Am Chem Soc 119 10,049 (c) Kobayashi S.Akiyama R, Kawamura M, Ishitani H (1997) Chem Lett 1039 (d) Kobayashi S, Ishitani H, Ueno M (1997) Synlett 115... [Pg.300]

Addition of carbon-centered radicals to imines and related compounds (heterocyclizations) 01T5461. [Pg.14]

Addition of Carbon-Centered Radicals to Imines and Related Compounds," Friestad. G.K. Tetrahedron, 2001, 57, 5461. [Pg.619]

Hydrogenation and Transfer Hydrogenation of Imines and Related Compounds... [Pg.53]

Chiral a-branched amines are common substructures within biologically active materials and hence attract broad interest, particularly in the areas of synthetic methodology, bioorganic and medicinal chemistry and natural product synthesis. Additions of carbon fragments to C=N bonds of imines and related compounds build up the carbon framework in the same way as asymmetric induction, so this approach is one of the more attractive entries to chiral amines. ... [Pg.123]

Propargylation/allenylation of carbonyls, imines, and related compounds... [Pg.116]

The pyridine-like nitrogens in imines and related compounds, as expected, lie at low shielding, and protonation induces a... [Pg.220]

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