An enantioselective synthesis of (S)-7-amino-5H, 7H-dibenzo[b,d]azepin-6-one (S-1) is described. The key step in the sequence involved crystallization-induced dynamic resolution (CIDR) of compound 7 using Boc-D-phenylalanine as a chiral resolving agent and 3,5-dichlorosalicylaldehyde as a racemization catalyst to afford S-1 in 81% overall yield with 98.5% enantiomeric excess.
Diastereoselective synthesis of (3R,4R)-4-acetoxy-3-[1 0 (R)-tert-butyldimethylsilyloxyethyl] azetidin-2-one (AOSA) using (-)-D-2,10-camphorsultam as a key and recyclable chiral auxiliary is described.
Antibiotics U 1200Novel Synthesis of (3R,4R)-4-Acetoxy-3-[1'(R)-tert-butyldimethylsilyloxyethyl] Azetidin-2-one: A Key Intermediate for Penem and Carbapenem Synthesis. -2,10-Camphorsultam is used as chiral auxiliary for a novel approach to title compound (XIII), a key intermediate in the industrial-scale synthesis of new-generation β-lactams. The Michael addition to (VII) and the last step to the targeted compound follows known procedures. -(SINGH, S. K.; SINGH, G. B.; BYRI, V. K.; SATISH, B.; DHAMJEWAR*, R.; GOPALAN, B.; Synth. Commun. 38 (2008) 3, 456-464; Matrix Lab. Ltd., Medak Dist, Jinnaram 502 325, India; Eng.) -H. Haber 28-204
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