Organocatalytic Asymmetric Michael Addition of 2,2-Dimethyl-1,3-dioxan-5-one to Nitro Alkenes Employing Proline-Based Catalysts

✍ Scribed by Dieter Enders; Sharon Chow

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 139 KB
• Volume: 2006
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200600464

✦ Synopsis

Abstract

The organocatalytic asymmetric Michael addition of 2,2‐dimethyl‐1,3‐dioxan‐5‐one (1) was performed with various nitro alkenes 2 using a number of proline‐based catalysts (A–M) affording polyfunctional nitro ketones 3. Reverse diastereoselectivity was observed with the diphenylprolinol catalyst J, and the best diastereo‐ and enantiomeric excesses were achieved with the sulfonamide catalyst M (de = 84–98 %, ee = 81–86 %). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)