Nucleophilic ring opening of trans-2, 3-disubstituted epoxides to β-amino alcohols with catalyst-controlled regioselectivity. Issue 92 (2nd November 2018)

• Record Type: Journal Article
• Authors: Lee, Michelle; Lamb, Jessica R.; Sanford, Maria J.; LaPointe, Anne M.; Coates, Geoffrey W.
• Is Part Of: Chemical communications. Volume 54:Issue 92(2018)
• Page Start: 12998
• Page End: 13001
• Publication Date: 2018-11-02
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c8cc07200k
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : We report the nucleophilic ring opening of unsymmetrical trans -epoxides to β-amino alcohols with catalyst-controlled regioselectivity. Abstract : We report the nucleophilic ring opening of unsymmetrical trans -epoxides to β-amino alcohols with catalyst-controlled regioselectivity. This cationic aluminum salen catalyst, which contains bulky mesityl groups in the ortho -position of the phenoxide and a 2, 2′-diamino-1, 1′-binaphthalene backbone, transforms a variety of epoxides with high regioselectivity using nitrogen-containing nucleophiles. Unlike most reports, in which regioselectivity is substrate controlled, the regioselectivity in this system is catalyst controlled and allows selective nucleophilic ring opening of unbiased trans -epoxides.