Work

Recrossing and Dynamic Matching Effects on Selectivity in a Diels–Alder Reaction

Year: 2009

Type: article

Abstract: Up and down the hill: The products from the hetero-Diels–Alder reaction of acrolein with methyl vinyl ketone arise from a single transition state (see scheme) and trajectory studies accurately predict the selectivity. In an extension of the dynamic matching idea of Carpenter, the product formed is determined by the direction of motion passing through the transition state. Recrossing occurs extensively and decreases formation of the minor product.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.200903293

Authors: Zhihong Wang, Jennifer S. Hirschi, Daniel A. Singleton

Institution: Texas A&M University

Language: English

Topic: Organic Chemistry Cycloaddition Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: Welch Foundation, National Institute of General Medical Sciences

Awards: New Concepts In Organic Selectivity and Mechanisms, G5812040939