Zinc(II)‐Catalyzed Intermolecular Hydrative Aldol Reactions of 2‐En‐1‐ynamides with Aldehydes and Water to form Branched Aldol Products Regio‐ and Stereoselectively1. (21st January 2015)

• Record Type: Journal Article
• Authors: Jadhav, Appaso Mahadev; Pagar, Vinayak Vishnu; Huple, Deepak B.; Liu, Rai‐Shung
• Is Part Of: Angewandte Chemie. Volume 127:Number 12(2015)
• Page Start: 3883
• Page End: 3887
• Publication Date: 2015-01-21
• Subjects: Aldolreaktionen -- Stereoselektivität -- Sulfonamide -- Synthesemethoden -- Zink; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201411689
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: This work describes zinc(II)‐catalyzed hydrative aldol reactions of 2‐en‐1‐ynamides with aldehydes and water to afford branched aldol products regio‐ and stereoselectively. The anti and syn selectivity can be modulated by the sizes of sulfonamides to yield E ‐ and Z ‐configured zinc(II) dienolates selectively. This new reaction leads to enantiopure aldol products by using a cheap chiral sulfonamide. The mechanistic analysis reveals that the sulfonamide amides of the substrates can trap a released proton to generate dual acidic sites to activate a carbonyl allylation reaction.