Diastereoselectivity in Passerini and Ugi reactions of chiral aldehydes/imines remains challenging. Moreover, the Ugi reaction of chiral acyclic imines is complicated by their easy racemization/epimerization, whereas this problem is nearly completely suppressed using chiral cyclic imines in a modification called Ugi-Joullié reaction. Thus 3-component modification also allows a better diastereoselectivity thanks to the higher steric rigidity of rings. This review presents an overview of the current knowledge on diastereoselective Passerini reaction of chiral aldehydes, and on diastereoselective Ugi-Joullié reaction of chiral cyclic imines, focusing on the results gathered by the authors' research group.
Diastereoselectivity in Passerini Reactions of Chiral Aldehydes and in Ugi Reactions of Chiral Cyclic Imines
Lambruschini C.;Moni L.;Banfi L.
2020-01-01
Abstract
Diastereoselectivity in Passerini and Ugi reactions of chiral aldehydes/imines remains challenging. Moreover, the Ugi reaction of chiral acyclic imines is complicated by their easy racemization/epimerization, whereas this problem is nearly completely suppressed using chiral cyclic imines in a modification called Ugi-Joullié reaction. Thus 3-component modification also allows a better diastereoselectivity thanks to the higher steric rigidity of rings. This review presents an overview of the current knowledge on diastereoselective Passerini reaction of chiral aldehydes, and on diastereoselective Ugi-Joullié reaction of chiral cyclic imines, focusing on the results gathered by the authors' research group.
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