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Enantioselective synthesis of (R)-tolterodine using lithiation/borylation–protodeboronation methodology
| Content Provider | PubMed Central |
|---|---|
| Author | Roesner, Stefan Aggarwal, Varinder K. |
| Abstract | The synthesis of the pharmaceutical (R)-tolterodine is reported using lithiation/borylation–protodeboronation of a homoallyl carbamate as the key step. This step was tested with two permutations: an electron-neutral aryl Li-carbamate reacting with an electron-rich boronic ester and an electron-rich aryl Li-carbamate reacting with an electron-neutral boronic ester. It was found that the latter arrangement was considerably better than the former. Further improvements were achieved using magnesium bromide in methanol leading to a process that gave high yield and high enantioselectivity in the lithiation/borylation reaction. The key step was used in an efficient synthesis of (R)-tolterodine in a total of eight steps in a 30% overall yield and 90% ee. |
| Starting Page | 965 |
| File Format | |
| ISSN | 14803291 |
| e-ISSN | 14803291 |
| Journal | Canadian journal of chemistry |
| Issue Number | 11 |
| Volume Number | 90 |
| Language | English |
| Publisher Date | 2012-11-01 |
| Access Restriction | Open |
| Subject Keyword | Research in Higher Education |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
