Regioselective Synthesis of Nitrones by Decarboxylative Oxidation of N-Alkyl-. ALPHA.-amino Acids and Application to the Synthesis of 1-Azabicyclic Alkaloids.

H Ohtake, Y Imada, SI Murahashi

Index: Ohtake, Hiroaki; Imada, Yasushi; Murahashi, Shun-Ichi Bulletin of the Chemical Society of Japan, 1999 , vol. 72, # 12 p. 2737 - 2754

Full Text: HTML

Citation Number: 59

Abstract

Tungstate-catalyzed oxidation of N-alkyl-α-amino acids with 30% H 2 O 2 solution under phase-transfer conditions gives nitrones regioselectively in good yields. Using this method, stereodivergent synthesis of (R)-and (S)-4-(t-butyldimethylsilyloxy)-1-pyrroline N-oxides ((R)- 17a and (S)-17a) was achieved. In addition,(R)-and (S)-3-(t-butyldimethylsilyloxy)-1- pyrroline N-oxides ((R)-45 and (S)-45) were prepared by catalytic oxidation of the ...