LiClO₄‐Catalyzed Highly Diastereoselective Synthesis of cis‐Aziridine Carboxylates.

Abstract

Aziridine derivativesAziridine derivatives R 0040 LiClO 4 -Catalyzed Highly Diastereoselective Synthesis of cis-Aziridine Carboxylates. -Aldimines, generated in situ from aldehydes (I) and amines (II), undergo ready addition with ethyl diazoacetate (III) in the presence of a catalytic amount of LiClO4 to afford the corresponding cis-aziridines (IV) in high yields and with high diastereoselectivity. -(YADAV*, J. S.; REDDY, B. V. S.; RAO, M. S.; REDDY, P. N.; Tetrahedron Lett. 44 (2003) 28, 5275-5278; Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 007, India; Eng.) -M. Paetzel 42-101

3-Arylaziridine-2-carboxylic Acid Derivatives and (3-Arylaziridin-2-yl)ketones: The Aziridination Approaches

“…Other simple catalysts for imine C=N bound aziridination with diazo compounds include BF 3 *OEt 2 [ 47 , 48 ], montmorillonite K-10 [ 49 ], LiClO 4 [ 50 ] and Rh 2 (OAc) 4 [ 44 , 51 ]. The Lewis acid BF 3 *OEt 2 -catalyzed reaction of imino ester 2d and phenyldiazomethane 3f produces the aziridine ester cis - 1a4 in good yield [ 47 ] without enamino- and dimeric byproducts ( Scheme 10 ).…”

“…The demonstrated procedure is very simple, namely, reactions were performed at room temperature with EDA as solvent [ 49 ]. A similar method with LiClO 4 catalysis allows to obtain broad spectrum (18 examples) of 3-aryl aziridine esters cis - 1a at room temperature in acetonitrile over 4.5–7.5 h at >75% chemical yields and good stereoselectivity [ 50 ].…”