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.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 12998-13001 |
| Number of pages | 4 |
| Journal | Chemical Communications |
| Volume | 54 |
| Issue number | 92 |
| DOIs | |
| State | Published - 2018 |
| Externally published | Yes |
Bibliographical note
Funding Information:This research was supported by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences, under Award DE-FG02-05ER15687. J. R. L. acknowledges a graduate fellowship from the National Science Foundation (DGE-1144153). This work made use of the NMR facility at Cornell University which is supported, in part, by the National Science Foundation (CHE-1531632). The authors would like to thank Dr Ivan Keresztes for his assistance in characterizing catalyst 1i.
Publisher Copyright:
© The Royal Society of Chemistry.