102423-80-3Relevant academic research and scientific papers
Silyllithium-Initiated Coupling of α-Ketoamides with tert-Butanesulfinylimines for Stereoselective Synthesis of Enantioenriched α-(Silyloxy)-β-amino Amides
Sun, Zhao,Liu, Hui,Zeng, Yong-Ming,Lu, Chong-Dao,Xu, Yan-Jun
, p. 620 - 623 (2016)
A silyllithium-initiated coupling of α-ketoamides with tert-butanesulfinylimines was developed for the efficient, stereoselective synthesis of enantioenriched α-(silyloxy)-β-amino amides. Nucleophilic addition of silyllithium to α-ketoamides, followed by 1,2-Brook rearrangement, generates nucleophilic enolates, which are then intercepted by chiral imines to provide three-component coupling products. Use of α-ketoamides is critical for achieving high yields and diastereoselectivities in the resulting α-hydroxy-β-amino acid derivatives.
Chemoselective Reductive Deoxygenation and Reduction of α-Keto Amides by using a Palladium Catalyst
Mamillapalli, N. Chary,Sekar, Govindasamy
, p. 3273 - 3283 (2015/11/03)
A palladium catalyst is used to synthesize 2,N-diphenylacetamides and α-hydroxy amides from readily available α-keto amides by chemoselective reductive deoxygenation and chemoselective reduction using polymethylhydrosiloxane (PMHS). This methodology has t
Metal free chemoselective reduction of α-keto amides using TBAF as catalyst
Mamillapalli, N. Chary,Sekar, Govindasamy
, p. 61077 - 61085 (2015/02/19)
The metal and ligand free chemoselective reduction of the keto group and complete reduction of the both keto and amide groups of α-keto amide with hydrosilanes using tetrabutylammoniumflouride (TBAF) as catalyst have been accomplished. This methodology affords an efficient and economic route for the synthesis of biologically important α-hydroxy amides and β-amino alcohols. The other important advantage of this TBAF catalyst is chemoselective reduction of ketones to corresponding alcohols in the presence of several other sensitive functional groups.
Asymmetric induction in the cycloaddition of a mandeloylnitroso compound and penta-1,3-diene: X-ray crystal structure analysis of two N-mandeloyldihydrooxazines
Freer, Andrew A.,Isaacs, Neil W.,Kirby, Gordon W.,Snedden, Peter,Tierney, Sean G. T.
, p. 601 - 621 (2007/10/03)
Oxidation of (+/-)-mandelohydroxamic acid with tetraethylammonium periodate in the presence of (E)-penta-1,3-diene at 0 deg C gave a mixture of 4 racemic cycloadducts of the derived, transient acylnitroso compound (+/-)-2.The 6-methyl 5 and 6 and 3-methyl 7 and 8 pairs of diastereoisomeric dihydro-oxazines were obtained in the ratio 3.0 : 1 : 1.2 :1.2 , respectively.The relative configurations of the racemic cycloadducts 5 and 7 were determined by X-ray crystallography.The relative asymmetric inductions observed for the pairs of regioisomers 5 and 6 and 7 and 8 are briefly discussed.
Carbmoyllithiums. A Novel Method for Generation by Lithium-Tellurium Exchange Reaction
Hiiro, Tomoki,Mogami, Toshiaki,Kambe, Nobuaki,Fujiwara, Shin-Ichi,Sonoda, Noboru
, p. 703 - 711 (2007/10/02)
Reaction of Te-butyl carbamotelluroates with butyllithium at low temperatures resulted in efficient transmetallation to give corresponding carbamoyllithiums.A convenient one-pot procedure for nucleophilic carbamoylation using carbamoyl halides has been developed as an application of this reaction.
New Reduction Method of α-Diketones, Oxo amides, and Quinones with Zn-EtOH in the Presence of a Salt
Toda, Fumio,Tanaka, Koichi,Tange, Hiroshi
, p. 1555 - 1556 (2007/10/02)
The reagent, Zn-Salt-EtOH effectively reduces α-diketones, oxo amides, and quinones to hydroxy ketones, hydroxy amides, and hydroquinones, respectively.
Direct Aminolysis of Nonactivated and Thermally Unstable Esters at High Pressure
Matsumoto, Kiyoshi,Hashimoto, Shiro,Uchida, Takane,Okamoto, Tadashi,Otani, Shinichi
, p. 1357 - 1364 (2007/10/02)
The preparation of the amides 3 from a wide variety of nonactivated esters 1 and secondary amines 2 has been achieved at 8 kbar and around 45 deg C; scope and limitations are discussed.The method was also successfully applied for the aminolysis of alkyl 2-arylsulfinylacetates 7 that are relatively sensitive to heat. - Key Words: Aminolysis/ High-pressure synthesis
