Ring Opening and Expansion of Aziridines in a Silica−Water Reaction Medium

Abstract

Ring-opening reactions of N-tosylaziridines with water-soluble nucleophiles proceeded in a silica-water reaction medium. The system is applicable to a ring expansion of an aziridine with potassium thiocyanate, leading to a thiazolidine derivative.

Aziridine Ring Opening: An Overview of Sustainable Methods

“…Minakata and co‐workers reported ring‐opening reactions of N ‐tosyl protected aziridines with water‐soluble nucleophiles with silica gel in water (Scheme ) . Various N‐tosylaziridines 20 reacted with KCN to produce N ‐tosyl protected cyano‐amines 22 with complete regioselectivity in good yields.…”

Organocatalyzed enantioselective desymmetrization of aziridines and epoxides

“…Many examples of the ring-opening of aziridines by various carbon [29–30], nitrogen [31–32], oxygen [33–34], sulfur [35–36] and halogen [37–39] nucleophilic reagents in the presence of catalytic amounts of small acids and bases such as BF 3 ·Et 2 O, AcOH, TsOH, TFA, PBu 3 , TMEDA, TBAF, Bu 4 NHSO 4 , pyridine N -oxide, and N -heterocyclic carbenes were published. However, the enantioselective ring-opening of meso -aziridines in the presence of chiral organocatalysts ( OC ) has emerged as a research field only in recent years.…”

Unprotected Aziridines: A Synthetic Overview

“…Aziridines are highly reactive molecules that serve as useful synthetic intermediates in several chemical transformations (Figure ). They can be converted into β‐amino alcohols or vicinal diamines, amongst others, through S N 2 ring‐opening reactions …”