Journal
SYNTHESIS-STUTTGART
Volume 49, Issue 3, Pages 657-666Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1588075
Keywords
asymmetric synthesis; chromans; catalysis; Heck reaction; Mitsunobu reaction; heterocycles
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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.
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