- Stereoselective allylation and reduction of N-tert-butanesulfinyl-α-keto aldimines
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A simple methodology for the synthesis of N-tert-butanesulfinyl-α-keto aldimines from both α-keto aldehydes and carboxylic esters has been developed. The addition of an in situ formed allyl indium reagent to these chiral imines was also studied. The addition took place in a sequential manner, first to the imine group with excellent diastereoselectivity and then to the carbonyl group with lower diastereoselectivity. Ruthenium-catalyzed ring closing metathesis of the resulting 5-aminoocta-1,7-dien-4-ol derivatives provided access to 6-aminocyclohex-3-enols. Reduction of the α-keto aldimines led to N-tert-butanesulfinyl-1,2-aminoalcohols as a 1:1 diastereomeric mixture.
- Maciá, Edgar,Foubelo, Francisco,Yus, Miguel
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p. 1407 - 1413
(2017/10/06)
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- A convenient synthesis of novel 2,8-disubstituted pyrido[3,4-b]pyrazines possessing biological activity
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A regioselective synthetic route to 2,8-disubstituted pyrido[3,4-b] pyrazines, by initial condensation reaction between suitable diaminopyridines and α-keto aldehydes equivalents, has been developed. Focusing on the functionalization on C-8, 2-aryl-8-bromo- and 8-amino-2-arylpyrido[3,4-b] pyrazines have been synthesized. Anilines, amides, and ureas have been introduced at the 8-position from key intermediates. 2,8-Disubstituted pyrido[3,4-b]pyrazines thus prepared were found to be of biological interest. Georg Thieme Verlag Stuttgart. New York.
- Antoine, Maud,Gerlach, Matthias,Guenther, Eckhard,Schuster, Tilmann,Czech, Michael,Seipelt, Irene,Marchand, Pascal
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- 6-(1-ACYL-1-HYDROXYMETHYL)PENICILLANIC ACID DERIVATIVES
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6-(1-Acyl-1-hydroxymethyl)penicillanic acid derivatives are useful as antibacterials and/or beta-lactamase inhibitors.
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- KINETIC STUDIES ON THE ACID-CATALYZED PUMMERER REACTION OF α-(METHYLSULFINYL)ACETOPHENONES
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The kinetic behavior of the acid catalyzed Pummerer reaction of α-(methylsulfinyl)acetophenones in dilute hydrochloric acid has been studied in detail.The kinetic data were amalyzed in the light of correlations between the reaction rates and acidity funct
- Kunieda, Norio,Fujiwara, Yoichi,Suzuki, Akira,Kinoshita, Masayoshi
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p. 223 - 232
(2007/10/02)
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