Miyuki Anzai

PALLADIUM-CATALYZED REGIO- AND STEREOSELECTIVE SYNTHESIS OF N-PROTECTED 2,4-DIALKYLATED AZACYCLOBUTANES FROM AMINO ALLENES

Abstract Palladium-catalyzed reaction of N-arylsulfonyl-1-alkyl-3,4-dienylamines with an aryl iodide in the presence of potassium carbonate in DMF at around 70°C affords most predominantly the 2,4-cis-disubstituted azacyclobutanes bearing an aryl group on the double bond in good yields.

Asymmetric synthesis of β2,3-amino acids by InI–Pd(0)-promoted metalation and addition of chiral 2-vinylaziridines

Abstract The reaction of optically active 3-alkyl-2-vinylaziridines with various aldehydes in the presence of InI and Pd(PPh 3 ) 4 gives rise to chiral syn , syn -2-vinyl-1,3-amino alcohols possessing three contiguous chiral centers stereoselectively. The ratio of the syn , syn -isomer to the other three isomers is significantly affected by the C3-substituents of aziridines as well as the alkyl groups of aldehydes. In addition, the obtained 1,3-aminoalcohols can be converted into biologically important β 2,3 -amino acid derivatives.

Stereoselective synthesis of nonracemic 1,3-amino alcohols from chiral 2-vinylaziridines by InI–Pd(0)-promoted metalation

Abstract Treatment of optically active 3-alkyl-2-vinylaziridines 1 , 8 and 9 and allylic acetates 10 and 11 with InI in the presence of Pd(PPh 3 ) 4 gives rise to chiral allylindiums bearing an amino group at the δ-position, which react with several aldehydes in highly regio- and stereoselective manner to afford the syn , syn -2-vinyl-1,3-amino alcohols 2a , 5a – 7a and 12a – 14a possessing three contiguous chiral centers in good yields.