Work

Diastereoselectivity in Diels-Alder Cycloadditions of Erythrose Benzylidene-acetal 1,3-Butadienes with Maleimides

Year: 2012

Type: article

Abstract: Maleimides were combined with d -erythrose benzylidene-acetal 1,3-butadienes to study the facial selectivity of the Diels–Alder cycloadditions. The selectivity was found to range from moderate to good. The reaction diastereotopicity can be reversed with the temperature. Simultaneous coordination of the diene, having a free hydroxy group, and maleimide to a chiral bimetallic Lewis acid catalyst (LACASA–DA reaction) occurs with complete diastereocontrol to give a single adduct, using an extra chiral inductor either ( R )- or ( S )-BINOL.

Source: Synlett

DOI: 10.1055/s-0031-1289785

Authors: Maria Alves, Daniela Salgueiro, Vera Duarte, Cristina Sousa, António Gil Fortes

Institutions: University of Minho, Centro de Química

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

OpenAlex ID: W2008944508

FWCI:

Cites:

Cited by: 2

Related to: 10