A Modular Synthesis of 2-Alkyl- and 2-Arylchromans via a Three-Step Sequence
| Autor: | Robert K. Orr, Harry R. Chobanian, Barbara Pio, Jamie M. McCabe Dunn, Louis-Charles Campeau, Rebecca T. Ruck, Andrew Nolting, Christopher W. Plummer |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
Allylic rearrangement Ketone 010405 organic chemistry Stereochemistry Organic Chemistry Enantioselective synthesis 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Reduction (complexity) chemistry.chemical_compound chemistry Heck reaction Mitsunobu reaction Derivative (chemistry) Alkyl |
| Zdroj: | Synthesis. 49:657-666 |
| ISSN: | 1437-210X 0039-7881 |
| Popis: | A convergent three-step method for the synthesis of 2-substituted chromans is described. These results have been accomplished via the Heck coupling of readily accessible allylic alcohols and 2-iodophenols, followed by reduction and Mitsunobu cyclization. The utility and generality of this method is demonstrated through the synthesis of a series of 2-aryl-, 2-heteroaryl- and 2-alkylchromans, as well as an azachroman derivative. The asymmetric version of this approach via a Noyori-catalyzed ketone reduction and subsequent cyclization is likewise highlighted. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|