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2005
Azetidine derivatives
R 0045
The Indium-Mediated Selective Introduction of Allenyl and Propargyl Groups at
C4-Position of 2-Azetidinones and the AuCl3-Catalyzed Cyclization of 4-Alle29- 113 the
nyl-2-azetidinones. — Organoindium reagents are generated in situ from γ-substituted
propargyl bromides, indium and KI in DMF. With 4-acetoxy-2-azetidinones they produce selectively the corresponding 4-allenyl-azetidinones in good to excellent yields.
Under analogous conditions, α-substituted propargyl bromides afford selectively
4-propargyl azetidinones. Gold(III) chloride is found to be an efficient catalyst for the
cyclization of azetidinones (III) to bicyclic lactams (IV). — (LEE*, P. H.; KIM, H.;
LEE, K.; KIM, M.; NOH, K.; KIM, H.; SEOMOON, D.; Angew. Chem., Int. Ed. 44
(2005) 12, 1840-1843; Dep. Chem., Kangwon Natl. Univ., Chun-Cheon 200-701,
S. Korea; Eng.) — Klein
2005
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