1,2-Asymmetric induction in nucleophilic Michael addition reactions of amines under microwave irradiation

Romanova, N. N.; Gravis, A.G.; Leshcheva, I. F.; Bundel, Yurii G.

doi:10.1070/mc1998v008n04abeh000970

Cited by 13 publications

(4 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1,2 asymmetric induction of up to 76 % diastereoisomeric excess was observed in reactions of several amines with b-substituted acrylic acid esters from d-(+)-mannitol, in the absence of solvent, after exposure to microwaves for 12 min [79]. …”

Section: Synthesis Of Alkyl P-toluenesulfinatesmentioning

confidence: 95%

Nonthermal Effects of Microwaves in Organic Synthesis

Perreux¹,

Loupy²

2002

Microwaves in Organic Synthesis

View full text Add to dashboard Cite

Section: Synthesis Of Alkyl P-toluenesulfinatesmentioning

confidence: 95%

Nonthermal Effects of Microwaves in Organic Synthesis

Perreux¹,

Loupy²

2002

Microwaves in Organic Synthesis

View full text Add to dashboard Cite

“…The initial failure led to the exploration of alternative conditions employing microwave technology. This choice was based on a number of studies indicating that microwaves are capable of accelerating a wide range of thermally driven reactions, including additions, cycloadditions, condensations, substitutions, rearrangements, organometallic reactions, and a host of others − . The application of microwave energy results in a very rapid transfer of energy to the reactant molecules enabling the activation energy to be reached quickly , .…”

Section: Introductionmentioning

confidence: 99%

Microwave-Mediated Synthesis of Labeled Nucleotides with Utility in the Synthesis of DNA Probes

et al. 2010

View full text Add to dashboard Cite

A novel method of linking haptens to deoxycytidine 5'-triphosphate via microwave-mediated bisulfate-catalyzed transamination with hydrazine has been developed. This method enables the tethering of small molecule haptens to dCTP via a discrete polyethylene glycol (PEG) spacer, yielding N(4)-aminodeoxycytidine 5'-triphosphate-dPEG-haptens. This synthetic approach employs microwave-catalyzed hydrazinolysis that enables the attachment of spacers via hydrazine linkages. The microwave-mediated introduction of this hydrazine handle provides a significant improvement in yield over those of published thermal methods. The microwave reaction was shown to be scalable, and the final product was amenable to labeling with a wide variety of haptens. The resulting nucleotide triphosphates, N(4)-aminodeoxycytidine 5'-triphosphate-dPEG-haptens, can serve as unique substrates for the enzyme-mediated labeling of DNA probes. The efficacy of incorporation of one such novel nucleotide, N(4)-aminodeoxycytidine 5'-triphosphate-dPEG(4)-DNP, has been demonstrated in nick translation labeling of HER2 and HPV probes. The labeled probes have been shown to be effective in visualizing their target genes in tissue.

show abstract

“…The important specific MW effect observed is consistent with mechanistic considerations; the dipolar TS is more polar, and therefore more stabilized by the field, than the GS. 1,2-Asymmetric induction of up to 76% diastereoisomeric excess was observed in reactions of several amines with β-substituted acrylic acid esters from d-(+)-mannitol, in the absence of solvent, after exposure to MWs for 12 min [150]. MW activation coupled with a dry media technique as a Green Chemistry procedure has been applied to the synthesis of a series of 1,5-benzothiazepines [151][152][153].…”

Section: Scheme 49mentioning

confidence: 99%