Chiral Isochalcogenourea‐Catalysed Enantioselective (4+2) Cycloadditions of Allenoates

Author:

Vogl Lukas S.1,Mayer Peter2,Robiette Raphaël3ORCID,Waser Mario1ORCID

Affiliation:

1. Institute of Organic Chemistry Johannes Kepler University Linz Altenbergerstrasse 69 4040 Linz Austria

2. Department Chemie Ludwig-Maximilians-Universität München Butenandtstraße 5–13 81377 München Germany

3. Institute of Condensed Matter and Nanosciences Université catholique de Louvain Place Louis Pasteur 1 box L4.01.02 1348 Louvain-la-Neuve Belgium

Abstract

AbstractAllenoates are versatile building blocks which are primarily activated and controlled using chiral tert. phosphine and tert. amine Lewis bases. We herein report the first example of allenoate activation by using chiral isochalcogenoureas (IChU) for formal (4+2) cycloaddition reactions. Compared to established phosphine and amine catalysis, the use of these easily available Lewis bases enables new stereoselective reaction pathways proceeding with high enantioselectivities, diastereoselectivities, and in good yields. In addition, the factors governing enantioselectivity and the origin of the observed differences compared to other commonly used Lewis bases are explained.

Publisher

Wiley

Subject

General Medicine

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