Transannular macrocyclization via intramolecular B-alkyl Suzuki reaction Journal Article
| Authors: | Chemler, S. R.; Danishefsky, S. J. |
| Article Title: | Transannular macrocyclization via intramolecular B-alkyl Suzuki reaction |
| Abstract: | (equation presented) Transannular macrocyclizations via intramolecular B-alkyl Suzuki reactions are described. Regioselective terminal olefin hydroboration with 9-BBN followed by Pd(0)-catalyzed Suzuki reaction in the presence of a base such as TIOEt at high dilution generates macrocycles with a high degree of control over olefin geometry with isomerically pure E or Z vinyl iodide substrates. These reactions are complementary to ring closing metathesis (RCM) macrocyclizations and may prove superior in cases where control of olefin geometry is required. |
| Keywords: | chemistry; cyclization; chemistry, organic; synthesis; ketone; ketones; organic chemistry; indicators and reagents; bridged compounds; cesium; dyes, reagents, indicators, markers and buffers; bridged compound; article |
| Journal Title: | Organic Letters |
| Volume: | 2 |
| Issue: | 17 |
| ISSN: | 1523-7060 |
| Publisher: | American Chemical Society |
| Date Published: | 2000-08-24 |
| Start Page: | 2695 |
| End Page: | 2698 |
| Language: | English |
| PUBMED: | 10990430 |
| PROVIDER: | scopus |
| DOI: | 10.1021/ol0062547 |
| DOI/URL: | |
| Notes: | Export Date: 18 November 2015 -- Source: Scopus |
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