Highly Enantioselective Addition of Diphenylzinc to Aliphatic and Aromatic Aldehydes Catalyzed by a Readily Available H8-Binol Derivative

✍ Scribed by Ying-Chuan Qin; Lin Pu

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 131 KB
• Volume: 118
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/ange.200503206

✦ Synopsis

Chiral a-substituted benzyl alcohols are ubiquitous in the structure of organic compounds. A straightforward synthesis of these compounds involves the nucleophilic addition of a phenyl-metal reagent to an aldehyde which produces a carbon-carbon bond and a stereogenic center simultaneously. Because of the high activity of phenyllithium and phenyl Grignard reagents, their asymmetric reactions with aldehydes need to be conducted in the presence of stoichiometric or excess amount of chiral reagents. [1][2][3][4][5] Among the catalytic asymmetric additions of the phenyl group to aldehydes, [6][7][8][9][10][11][12][13][14][15][16] the use of diphenylzinc has received much attention in recent years as the reagent is readily available. [10][11][12][13][14][15][16] In 1997, Fu and co-workers reported the addition of diphenylzinc to aldehydes catalyzed by 1 with