Asymmetric control in Diels–Alder cycloadditions of chiral 9-aminoanthracenes by relay of stereochemical information

H Adams, RA Bawa, KG McMillan, S Jones

Index: Adams, Harry; Bawa, Ramadan A.; McMillan, Keith G.; Jones, Simon Tetrahedron Asymmetry, 2007 , vol. 18, # 8 p. 1003 - 1012

Full Text: HTML

Citation Number: 28

Abstract

Two approaches to the synthesis of chiral 9-amino anthracenes are described. The first, by nucleophilic addition of organolithium reagents to imines promoted by BF3· OEt2, unexpectedly provided stable aminoboranes as products. The second approach, using palladium catalysed cross coupling, was more successful for primary amines, and the key 9- (α-methylbenzylamino) anthracene subjected to cycloadditions with N-methyl maleimide ...