Work

Intermolecular Michael Reactions: A Computational Investigation

Year: 2010

Type: article

Abstract: Computational studies have suggested that η(3)-lithium enolates in which the cation is partially bound to both carbon and oxygen may be important reactive intermediates. DFT calculations are used to demonstrate that explicitly solvated acetone enolates are largely O-bound. With this premise in mind, the stereochemical course of intermolecular Michael additions is examined. The results are generally consistent with what is observed experimentally and the model advanced by Heathcock and co-workers.

Source: Organic Letters

DOI: 10.1021/ol102017v

Authors: Eugene E. Kwan, David A. Evans

Institution: Harvard University

Language: English

Topic: Coordination Chemistry and Organometallics

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: Synthesis of Polyketides and Terpenes, G1630477216