Bifunctional Guanidine via an Amino Amide Skeleton for Asymmetric Michael Reactions of β-Ketoesters with Nitroolefins: A Concise Synthesis of Bicyclic β-Amino Acids

✍ Scribed by Zhipeng Yu; Xiaohua Liu; Lin Zhou; Lili Lin; Xiaoming Feng

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 445 KB
• Volume: 48
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.200901337

✦ Synopsis

Abstract

Two activations are better than one: The chiral bifunctional guanidine 1, which features an amino amide backbone, catalyzes the asymmetric Michael addition of a range of substrates and gives products with excellent stereoselectivities. The method also allows the efficient synthesis of optically pure β‐amino acid esters. Both the guanidine group and the NH proton of the amide were important for the dual activation.magnified image