Work

N-Heterocyclic Carbene-Initiated α-Acylvinyl Anion Reactivity: Additions of α-Hydroxypropargylsilanes to Aldehydes

Year: 2007

Type: article

Abstract: Highly substituted alpha,beta-unsaturated ketones are prepared by the N-heterocyclic carbene-initiated addition of alpha-hydroxypropargylsilanes to aldehydes. This strategy serves as a highly efficient alternative to the standard Morita-Baylis-Hillman (MBH) approaches for these types of compounds. In contrast to the MBH reaction, different substitution in the beta-position of the product (R1) can be accommodated in moderate to excellent yields with a high degree of control over the resulting alkene.

Source: Organic Letters

DOI: 10.1021/ol0710515

Authors: Troy E. Reynolds, Charlotte A. Stern, Karl A. Scheidt

Institution: Northwestern University

Language: English

Topic: N-Heterocyclic Carbenes in Organic and Inorganic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Amgen, National Institute of General Medical Sciences, Division of Chemistry

Award: G682315649