ChemInform Abstract: A Chiral, Oxidatively Cleavable Auxiliary in β-Lactam Synthesis — Double Diastereocontrol with p-Methoxyphenethyl-Substituted Imines.

✍ Scribed by Joachim Podlech; Steffen Steurer

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 31 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199931127

✦ Synopsis

A Chiral, Oxidatively Cleavable Auxiliary in β-Lactam Synthesis -Double Diastereocontrol with p-Methoxyphenethyl-Substituted Imines.

-Photolysis of the chiral diazoketones (I) generates chiral ketenes. These react in situ with the (S)-imine (II) to yield the transsubstituted β-lactams (III) and (IV) by double stereoselection. The chiral p-methoxyphenylethyl auxiliary can be removed with cerium ammonium nitrate as shown for (IIIa).