Work

Lewis Acid Activated Synthesis of Highly Substituted Cyclopentanes by the N‐Heterocyclic Carbene Catalyzed Addition of Homoenolate Equivalents to Unsaturated Ketoesters

Year: 2011

Type: article

Abstract: A great team: Cyclopentanes with four contiguous stereogenic centers were assembled with excellent diastereo- and enantioselectivity from simple β,γ-unsaturated α-ketoesters and enals in a reaction catalyzed by an N-heterocyclic carbene (NHC) and mediated by a titanium(IV) Lewis acid (see scheme). The presence of a Lewis acid was essential for the desired transformation to occur.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201005908

Authors: Daniel T. Cohen, Benoit Cardinal‐David, Karl A. Scheidt

Institutions: Northwestern University, Chemistry of Life Processes Institute

Language: English

Topic: N-Heterocyclic Carbenes in Organic and Inorganic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G344074598, G682315649