| Title | The crucial role of the nitrogen substituent in the desymmetrisation of cyclic meso-imides using B-Me and B-OMe oxazaborolidine catalysts |
| Publication Type | Journal Article |
| Year of Publication | 2006 |
| Authors | Barker, M.D., Dixon R.A., Jones S., and Marsh B.J. |
| Journal | Tetrahedron |
| Volume | 62 |
| Issue | 50 |
| Pagination | 11663 - 11669 |
| Date Published | 2006 |
| ISSN | 00404020 (ISSN) |
| Keywords | article, catalysis, enantioselectivity, high performance liquid chromatography, imide, priority journal, Reduction, substitution reaction |
| Abstract | Various cyclic meso-imides have been desymmetrised via enantioselective reduction using two chiral oxazaborolidine catalysts derived from (1R,2S)-cis-1-amino-indan-2-ol followed by the reduction of the hydroxylactam product to give the γ-lactam. The enantiomeric excesses were shown to be 27-99% by chiral HPLC and chiral GC of the γ-lactam products with the nitrogen substituent playing a pivotal role in determining yield and selectivity. © 2006 Elsevier Ltd. All rights reserved. |
| URL | http://www.scopus.com/inward/record.url?eid=2-s2.0-33751162111&partnerID=40&md5=b99d346984dec6f61a8f0a88a5254f31 |
| DOI | 10.1016/j.tet.2006.09.051 |
