The first example of chiral induction using homochiral boronic esters in the Petasis reaction

✍ Scribed by Tobias Koolmeister; Mikael Södergren; Martin Scobie

• Book ID: 104251645
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 114 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)01263-7

✦ Synopsis

The present study demonstrates the first enantioselective version of the Petasis reaction (boronic Mannich reaction), using glyoxylic acid, morpholine and a homochiral boronic ester as the chiral auxiliary. Chiral boronic esters are readily prepared by condensation of vinylboronic acids and chiral 1,2-diols. In the resulting Petasis reaction, 2-morpholin-1-yl-4-phenylbut-3-enoic acids are formed in high yields and moderate enantioselectivity.