Synthesis of C1-alkyl- and acylglycals from glycals using a B-alkyl Suzuki-Miyaura cross coupling approach Journal Article
| Authors: | Potuzak, J. S.; Tan, D. S. |
| Article Title: | Synthesis of C1-alkyl- and acylglycals from glycals using a B-alkyl Suzuki-Miyaura cross coupling approach |
| Abstract: | A B-alkyl Suzuki-Miyaura cross coupling approach provides a flexible, efficient means to convert glycals to C1-alkylglycals and C1-acylglycals that are versatile synthetic intermediates. This approach uses readily available glycal starting materials and overcomes major limitations associated with direct alkylation or acylation of glycals. Further, a commonly observed side reaction involving reduction of the halide coupling partner is suppressed by preincubation of the borane coupling partner with aqueous base, providing new mechanistic insights into the side reaction. © 2003 Elsevier Ltd. All rights reserved. |
| Keywords: | unclassified drug; chemical analysis; alkylation; technique; reaction analysis; reagent; chemical modification; alkyl group; cross coupling reaction; acylation; cross coupling; suzuki reaction; article; b-alkyl suzuki-miyaura; c-glycoside; glycal; borane derivative; suzuki miyauri cross coupling approach; lateolabrax japonicus |
| Journal Title: | Tetrahedron Letters |
| Volume: | 45 |
| Issue: | 8 |
| ISSN: | 0040-4039 |
| Publisher: | Pergamon-Elsevier Science Ltd |
| Date Published: | 2004-02-16 |
| Start Page: | 1797 |
| End Page: | 1801 |
| Language: | English |
| DOI: | 10.1016/j.tetlet.2003.12.006 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Tetrahedron Lett. -- Cited By (since 1996):32 -- Export Date: 16 June 2014 -- CODEN: TELEA -- Source: Scopus |
