Work

Lewis Acid-Catalyzed Conjugate Additions of Silyloxyallenes: A Selective Solution to the Intermolecular Rauhut−Currier Problem

Year: 2008

Type: article

Abstract: Silyloxyallenes serve as highly useful alpha-acylvinyl anion equivalents. These latent allenolates undergo conjugate additions to alkylidene malonates in the presence of 10 mol % Sc(OTf) 3. The reaction delivers intermolecular Rauhut-Currier products in excellent yields and regioselectivities for a wide scope of substrates. Notably, the formal cross-coupling of two different alpha,beta-unsaturated carbonyl compounds (a cross Rauhut-Currier reaction) is achieved. Preliminary investigations have demonstrated good levels of enantioselectivity for the addition of a racemic silyloxyallene with a chiral Lewis acid.

Source: Organic Letters

DOI: 10.1021/ol800745q

Authors: Troy E. Reynolds, Michael S. Binkley, Karl A. Scheidt

Institution: Northwestern University

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Amgen, AstraZeneca, GlaxoSmithKline, National Institute of General Medical Sciences

Awards: G388657058, G682315649