Asymmetric Conjugate Addition of Unmodified Propionaldehyde to β- Nitrostyrenes Catalyzed by Readily Available Proline-Based Dipeptidols

Title: Asymmetric Conjugate Addition of Unmodified Propionaldehyde to β- Nitrostyrenes Catalyzed by Readily Available Proline-Based Dipeptidols

Volume: 6 Issue: 1

Author(s): Ren-Yong Yang, Chao-Shan Da, Lei Yi, Feng-Chun Wu and Hong Li

Affiliation:

Keywords: Asymmetric conjugate addition, propionaldehyde, β-nitrostyrene, proline-based dipeptidol, organocatalysis, enantioselectivity

Abstract: Organocatalytic asymmetric additions of unmodified aldehydes to β-nitrostyrenes are important carbon-carbon bond formation reactions and have become very attractive recently, because they are metal-free and environmentally benign. This work employed a series of L-proline-based diphenyl dipeptidols to catalyze this reaction. The results showed that these dipeptidols were effective organocatalysts with the yield up to 99%. 3a was optimal with the highest enantioselectivity up to 75% and dr (syn/anti) up to 94/6. In addition, the mechanism of this asymmetric reaction is also discussed.

Cite this article as:

Yang Ren-Yong, Da Chao-Shan, Yi Lei, Wu Feng-Chun and Li Hong, Asymmetric Conjugate Addition of Unmodified Propionaldehyde to β- Nitrostyrenes Catalyzed by Readily Available Proline-Based Dipeptidols, Letters in Organic Chemistry 2009; 6 (1) . https://dx.doi.org/10.2174/157017809787003061