85390-54-1

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• 100-46-9 benzylamine 
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• 100-39-0 benzyl bromide 
• 541-47-9 3-Methylbutenoic acid 

Relevant academic research and scientific papers

Enantioselective Synthesis of Cyclopropanone Equivalents and Application to the Formation of Chiral β-Lactams

Cyclopropanone derivatives have long been considered unsustainable synthetic intermediates because of their extreme strain and kinetic instability. Reported here is the enantioselective synthesis of 1-sulfonylcyclopropanols, as stable yet powerful equivalents of the corresponding cyclopropanone derivatives, by α-hydroxylation of sulfonylcyclopropanes using a bis(silyl) peroxide as the electrophilic oxygen source. This work constitutes the first general approach to enantioenriched cyclopropanone derivatives. Both the electronic and steric nature of the sulfonyl moiety, which serves as a base-labile protecting group and confers crystallinity to these cyclopropanone precursors, were found to have a crucial impact on the rate of equilibration to the corresponding cyclopropanone. The utility of these cyclopropanone surrogates is demonstrated in a mild and stereospecific formal [3+1] cycloaddition with simple hydroxylamines, leading to the efficient formation of chiral β-lactam derivatives.

Highly selective intramolecular carbene insertion into primary C-H bond of α-diazoacetamides mediated by a (p-cymene)ruthenium(II) carboxylate complex

Complex [(p-cymene)Ru(η1-O2CCF3) 2(OH2)] mediated transformation of α-diazoacetamides ArCH2N(C(CH3)3)C(O)CHN2 to result in carbene insertion into the primary C-H bond exclusively, with the γ-lactam products being isolated in up to 98% yield. This unexpected reaction is striking in view of the presence of usually more reactive sites such as secondary C-H bonds in the substrates. DFT calculations based on proposed Ru-carbene species provide insight into this unique selectivity.

Diruthenium(I,I) catalysts for the formation of β- and γ-lactams via carbenoid C-H insertion of α-diazoacetamides

Intramolecular carbenoid C-H insertion of five α-diazoacetamides [N2CH-CONR2, NR2 = NEt2 (3a), NBu2 (3b), N(i-Pr)2 (3c), N(CH2Ph)2 (3d), N(i-Pr)(CH2Ph) (3e)], was investigated using as catalysts dinuclear Ru(I,I) complexes of the type [Ru2-(μ-L 1)2(CO)4L22], where L1 is a bidentate bridging acetate, calix[4]arenedicarboxylate, saccharinate, pyridin-2-olate, or triazenide ligand, as well as [RuCl 2(p-cymene)]2. The Ru(I,I) complexes were found to be suitable catalysts for the carbenoid cyclization reactions, except in the case of 3a. With diazoamides 3b-e, [Ru2(μ-sac)2(CO) 5]2 (sac=saccharinate) and [Ru2(μ-6- chloropyridin-2-olate)2(CH3CN)2(CO) 4] are as effective as Rh2(OAc)4 under the same conditions, although some differences in the regioselectivity and chemoselectivity of the cyclization are observed. The carbenoid cyclization reactions yield γ-lactams from diazoamides 3a and 3b, both a β- and a γ-lactam from 3c, and a β-lactam as well as a 3-azabicyclo-[5.3.0] deca-5,7,9-trien-2-one from 3d. With 3e, formation of γ-lactam 21 and of bicyclic lactam 23 prevails.

A facile synthesis of β-lactams by the cyclization of β-amino acids exploiting 3,3′-(phenylphosphoryl)-bis(1,3-thiazolidine-2-thione)

3,3′-(Phenylphosphoryl)-bis(1,3-thiazolidine-2-thione) (5), obtained from phenylphosphonic dichloride (7) and sodium salt of 1,3-thiazolidine-2-thione (6), proved to be useful for intramolecular dehydration of various β-amino acids to give the correspondi

NEW METHODS FOR β-LACTAM FORMATION FROM β-AMINO ACIDS USING (C6H5)3/CCl4 AND (C6H5)3P/NBS

Triphenylphosphine/carbon tetrachloride and triphenylphosphine/N-bromosuccinimide were found to be very effective for β-lactam formation from β-amino acids in acetonitrile.

A Convenient Method for β-Lactam Formation from β-Amino Acids using Diphenylphosphinic Chloride

Diphenylphosphinic chloride is found to be very effective in promoting β-lactam formation from β-amino acids.

A NEW CONVENIENT METHOD FOR β-LACTAM FORMATION FROM β-AMINO ACIDS USING BIS(5'-NITRO-2'-PYRIDYL) 2,2,2-TRICHLOROETHYL PHOSPHATE

Bis(5'-nitro-2'-pyridyl) 2,2,2-trichloroethyl phosphate is found to be a new efficient condensing agent for β-lactam formation from β-amino acids in acetonitrile.

MICHAEL-TYPE ADDITIONS TO α,β-ENOYLIRON(CYCLOPENTADIENYL)DICARBONYL COMPLEXES AND ITS APPLICATION TO β-LACTAM SYNTHESIS

Michael-type additions of amines and thiols to α,β-enoyliron(cyclopentadienyl)dicarbonyl complexes were carried out to give the corresponding new β-aminoalkanoyl- and β-thioalkanoyliron complexes in good to excellent yields.A β-aminoalkanoyliron complex w