60436-55-7Relevant academic research and scientific papers
Combination of Enabling Technologies to Improve and Describe the Stereoselectivity of Wolff-Staudinger Cascade Reaction
Musio,Mariani,?liwiński,Kabeshov,Odajima,Ley
, p. 3515 - 3526 (2016)
A new, single-mode bench-top resonator was evaluated for the microwave-assisted flow generation of primary ketenes by thermal decomposition of α-diazoketones at high temperature. A number of amides and β-lactams were obtained by ketene generation in situ and reaction with amines and imines, respectively, in good to excellent yields. The preferential formation of trans-configured β-lactams was observed during the [2+2] Staudinger cycloaddition of a range of ketenes with different imines under controlled reaction conditions. Some insights into the mechanism of this reaction at high temperature are reported, and a new web-based molecular viewer, which takes advantage from Augmented Reality (AR) technology, is also described for a faster interpretation of computed data.
One-pot synthesis of trans-β-lactams from ferrocenylketene generated by thermal Wolff rearrangement
Liu, Mingshun,Wang, Jian’an,Yuan, Xiaoxi,Jiang, Rong,Fu, Nanyan
, p. 2369 - 2377 (2017/12/12)
A series of β-lactams containing the ferrocene moiety were synthesized through the Staudinger reaction between ferrocenylketene generated by the thermal Wolff rearrangement of the corresponding diazo ketone and various imines. The stereochemical outcome h
Rhodium-catalyzed oxygenative [2 + 2] cycloaddition of terminal alkynes and imines for the synthesis of β-lactams
Kim, Insu,Roh, Sang Weon,Lee, Dong Gil,Lee, Chulbom
supporting information, p. 2482 - 2485 (2014/05/20)
A rhodium-catalyzed oxygenative [2 + 2] cycloaddition of terminal alkynes and imines has been developed, which gives β-lactams as products with high trans diastereoselectivity. In the presence of a Rh(I) catalyst and 4-picoline N-oxide, a terminal alkyne is converted to a rhodium ketene species via oxidation of a vinylidene complex and subsequently undergoes a [2 + 2] cycloaddition with an imine to give rise to the 2-azetidinone ring system. Mechanistic studies suggest that the reaction proceeds through a metalloketene rather than free ketene intermediate. The new method taking advantage of catalytic generation of a ketene species directly from a terminal alkyne provides a novel and efficient entry to the Staudinger synthesis of β-lactams under mild conditions.
Reagents and Synthetic Methods. Part 58. Synthesis of β-Lactams from Acetic Acids and Imines promoted by Vilsmeier Type Reagents
Arrieta, Ana,Lecea, Begona,Palomo, Claudio
, p. 845 - 850 (2007/10/02)
The development of a practical method for the stereospecific preparation of several 3-substituted β-lactams from acetic acids and imines is described.The key step of the method is the activation of the carboxy component by means of Vilsmeier type reagents.The preparation of some N-(2'-hydroxyethyl)-β-lactams and N-(p-dimethyl-t-butylsiloxyphenyl)-β-lactams as intermediates for N-H azetidinones is also reported.For the last compounds the steric bulk of the N-substituent is the key feature for a high cis-β-lactam formation.
N,N-DIMETHYLPHOSPHORAMIDIC DICHLORIDE: A CONVENIENT REAGENT FOR THE PREPARATION OF β-LACTAMS FROM ACETIC ACIDS AND IMINES
Cossio, Fernando P.,Ganboa, Inaki,Garcia, Jesus M.,Lecea, Begona,Palomo, C.
, p. 1945 - 1948 (2007/10/02)
A convenient reagent for the preparation of β-lactams from acetic acids and imines is described.A new route to α-keto-β-lactams from 3-bis(ethylthio)β-lactams is also reported.Reaction of 4-acethyl-β-lactams with diazomethane is also made.
TRIPHENYLPHOSPHINE DIBROMIDE AND DIMETHYLSULFIDE DIBROMIDE AS VERSATILE REAGENTS FOR BETA-LACTAM SYNTHESIS
Cossio, Fernando P.,Ganboa, Inaki,Palomo, Claudio
, p. 3041 - 3044 (2007/10/02)
Triphenylphosphine dibromide and dimethylsulfide dibromide are efficient reagents for the direct synthesis of beta-lactams from carboxylic acids and imines avoiding the use of acid halides as starting materials.Synthesis of 4-imino-beta-lactams are also briefly described.A potential synthesis of N-unsubstituted beta-lactams is made.
N,N-DIMETHYLCHLOROSULFITEMETHAMINIUM CHLORIDE (SOCl2-DMF) A VERSATILE DEHYDRATING REAGENT.
Arrieta, A.,Aizpurua, J. M.,Palomo, C.
, p. 3365 - 3368 (2007/10/02)
N,N-dimethylchlorosulfitemethaminium chloride formed from thionyl chloride and dimethylformamide was found and efficient reagent for the synthesis of acyl azides from carboxylic acids and nitriles from oximes.It is also highly efficient for the direct synthesis of beta-lactams from carboxylic acids and imines avoiding the use of acid chlorides.
