Density Functional Study of Organocatalytic Cross-Aldol Reactions between Two Aliphatic Aldehydes: Insight into Their Functional Differentiation and Origins of Chemo- and Stereoselectivities

• Published in: The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Vol. 117; no. 13; pp. 2862 - 2872
• Main Authors: Fu, Aiping, Zhao, Chengyan, Li, Hongliang, Tian, Fenghui, Yuan, Shuping, Duan, Yunbo, Wang, Zonghua
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 04.04.2013
• Subjects: Aldehydes; Aldehydes - chemistry; Aliphatic compounds; Amines - chemistry; Atomic and molecular physics; Calculations and mathematical techniques in atomic and molecular physics (excluding electron correlation calculations); Catalysis; Catalysts; Chemistry; Computer Simulation; Density; Density-functional theory; Electronic structure of atoms, molecules and their ions: theory; Electronics; Exact sciences and technology; Formations; Kinetics and mechanisms; Models, Molecular; Organic chemistry; Physics; Proline; Proline - chemistry; Quantum Theory; Reactivity and mechanisms; Stereoisomerism; Stereoselectivity; Thermodynamics; Geometrical structure; Stereoselectivity; Catalytic reaction; Transition state; Theoretical study; Reaction mechanism; Density functional method; Proline

The chemo-, diastereo-, and enantioselectivities in proline and axially chiral amino sulfonamide-catalyzed direct aldol reactions between two enolizable aldehydes with different electronic nature have been studied with the aid of density functional theory (DFT) method. The potential energy profiles...