A Modular Synthesis of 2-Alkyl- and 2-Arylchromans via a Three-Step Sequence.

Autor: Orr, Robert K., Campeau, Louis-Charles, Chobanian, Harry R., McCabe Dunn, Jamie M., Pio, Barbara, Plummer, Christopher W., Nolting, Andrew, Ruck, Rebecca T.
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Zdroj: Synthesis; 2017, Vol. 49 Issue 3, p657-666, 10p, 5 Diagrams, 3 Charts
Abstrakt: 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. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index