Facile stereoselective synthesis of cis-and trans-3-alkoxyazetidin-2-ones
A Bhalla, P Venugopalan, SS Bari
Index: Bhalla, Aman; Venugopalan, Paloth; Bari, Shamsher S. Tetrahedron, 2006 , vol. 62, # 35 p. 8291 - 8302
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Citation Number: 31
Abstract
A highly stereoselective synthesis of cis-and trans-3-alkoxy-3-phenyl/benzylthioazetidin-2- ones is described. The reaction of α-chlorosulfide-β-lactams with various alcohols catalyzed by a Lewis acid such as ZnCl2 in the presence of molecular sieves (3–4Å) leads to cis-3- alkoxy-3-phenyl/benzylthio-β-lactams whereas treatment of potassium 2-alkoxy-2- phenylthioethanoate with appropriate Schiff's base using POCl3 in the presence of ...
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