Journal of the American Chemical Society, Vol.116, No.22, 9927-9934, 1994
Synthesis of Optically-Active 4-Substituted 2-Aminobutyrolactones and Homoserines by Combined Aldol/Photocyclization Reactions of Chromium Aminocarbene Complexes
Aldol reactions of optically active chromium aminocarbene complexes proceeded with moderate to high diastereoselectivity. Photolysis of the aldol product gave optically active 4-substituted 2-aminobutyrolactones which could be hydrolyzed to gamma-hydroxy-alpha-amino acids. Using this procedure, (+)-bulgecenine was synthesized.
Keywords:ALPHA-AMINO-ACIDS;ASYMMETRIC-SYNTHESIS;CARBENE COMPLEXES;STEREOSELECTIVE SYNTHESIS;BETA-LACTAMS;PHOTOLYTIC REACTIONS;KETENE COMPLEXES;PEPTIDE;GLUCURONOLACTONE;(-)-BULGECININE