Direct asymmetric N-specific reaction of nitrosobenzene with aldehydes catalyzed by a chiral primary amine-based organocatalyst

✍ Scribed by Long Qin; Lei Li; Lei Yi; Chao-Shan Da; Yi-Feng Zhou

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 240 KB
• Volume: 23
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/chir.20960

✦ Synopsis

Abstract

Nitroso compounds have two reactive nitrogen and oxygen atoms. It is interesting and important to perform a nitrogen or oxygen selective reaction with interesting substrates. These atom specific reactions are crucial to specifically synthesis of specific compounds. An enantioselective N‐specific reaction of nitrosobenzene with unmodified aldehydes was successfully achieved catalyzed first by a variety of primary amine‐based organocatalysts with higher yield and enantioselectivity. The bulkier substituted groups of the organocatalyst and two hydrogen bonds from the organocatalyst and the oxygen atom of nitrosobenzene make the reaction preferentially N‐specific and predominantly afford R products. Chirality, 2011. © 2011 Wiley‐Liss, Inc.