Highly Efficient Asymmetric [3+2] Cycloaddition Promoted by Chiral Aziridine-Functionalized Organophosphorus Compounds
Julia Szymańska, Michał Rachwalski, Adam M. Pieczonka
TL;DR
This paper describes a highly efficient asymmetric [3+2] cycloaddition reaction using chiral organophosphorus compounds to form specific stereoisomers.
Contribution
The study introduces chiral aziridine-functionalized organophosphorus compounds as effective catalysts for asymmetric [3+2] cycloadditions.
Findings
Three out of sixteen possible stereoisomers were formed in the reaction.
Two stereoisomers were obtained in enantiomerically enriched or pure form.
One product underwent epimerization under basic conditions.
Abstract
The asymmetric [3+2] cycloaddition of azomethine ylides generated from the corresponding imino ester-to-trans-β-nitrostyrene catalysis by chiral aziridine-containing phosphines and phosphine oxides is described. Of the sixteen stereoisomers that could be formed as a result of the title reaction, three were formed, two of which were obtained in an enantiomerically enriched or pure form, and one in a racemic form. One of the products underwent epimerization under basic reaction conditions.
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Taxonomy
TopicsSynthesis and Catalytic Reactions · Asymmetric Synthesis and Catalysis · Advanced Synthetic Organic Chemistry