141694-26-0Relevant articles and documents
The photochemistry of N-p-toluenesulfonyl peptides: The peptide bond as an electron donor
Hill, Roger R.,Moore, Sharon A.,Roberts, David R.
, p. 1439 - 1446 (2008/02/01)
The scope of photobiological processes that involve absorbers within a protein matrix may be limited by the vulnerability of the peptide group to attack by highly reactive redox centers consequent upon electronic excitation. We have explored the nature of this vulnerability by undertaking comprehensive product analyses of aqueous photolysates of 12 N-p-toluene-sulfonyl peptides with systematically selected structures. The results indicate that degradation includes a major pathway that is initiated by intramolecular electron transfer in which the peptide bond serves as electron donor, and the data support the likelihood' of a relay process in dipeptide derivatives.
Catalytic asymmetric epoxidation of α,β-unsaturated amides: Efficient synthesis of β-aryl α-hydroxy amides using a one-pot tandem catalytic asymmetric epoxidation - Pd-catalyzed epoxide opening process
Nemoto, Tetsuhiro,Kakei, Hiroyuki,Gnanadesikan, Vijay,Tosaki, Shin-Ya,Ohshima, Takashi,Shibasaki, Masakatsu
, p. 14544 - 14545 (2007/10/03)
The catalytic asymmetric epoxidation of α,β-unsaturated amides using Sm-BINOL-Ph3As=O complex was succeeded. Using 5-10 mol % of the asymmetric catalyst, a variety of amides were epoxidized efficiently, yielding the corresponding α,β-epoxy amides in up to 99% yield and in more than 99% ee. Moreover, the novel one-pot tandem process, one-pot tandem catalytic asymmetric epoxidation-Pd-catalyzed epoxide opening process, was developed. This method was successfully utilized for the efficient synthesis of β-aryl α-hydroxy amides, including β-aryllactyl-leucine methyl esters. Interestingly, it was found that beneficial modifications on the Pd catalyst were achieved by the constituents of the first epoxidation, producing a more suitable catalyst for the Pd-catalyzed epoxide opening reaction in terms of chemoselectivity. Copyright
α-Keto Amides and 1,2-Diketones from N,N'-Dimethoxy-N,N'-dimethylethanediamide. A Synthetic and Mechanistic Investigation
Sibi, Mukund P.,Marvin, Mali,Sharma, Rajiv
, p. 5016 - 5023 (2007/10/03)
N,N'-Dimethoxy-N,N'-dimethylethanediamide (1), a 1,2-dicarbonyl synthon prepared from oxalyl chloride, undergoes nucleophilic displacements with Grignard reagents to provide α-keto amides 2-12 in 28-90percent yields.The synthon also undergoes double nucleophilic displacements with organolithium reagents to furnish symmetrical 1,2-diketones 15-23 in 15-84percent yields.A mechanism accounting for all the products from the reaction of 1 with nucleophiles has been proposed.Several control experiments were carried out to support the proposed mechanism.
N,N'-Dimethoxy-N,N'-dimethylethanediamide: A useful α-oxo-N-methoxy-N-methylamide and 1,2-diketone synthon
Sibi,Sharma,Paulson
, p. 1941 - 1944 (2007/10/02)
N,N'-Dimethoxy-N,N'-dimethylethanediamide on treatment with one to two equivalents of alkyl, aryl, and benzyl Grignard reagents provide α-oxo-N-methoxy-N-methylamides in good to excellent yields and on reaction with excess aryllithiums furnish moderate to good yields of symmetrical 1,2-diarylketones.