Asymmetric synthesis of hydrobenzofuranones via desymmetrization of cyclohexadienones using the intramolecular Stetter reaction.
Dearomatization of phenols followed by oxidation affords cyclohexadienyloxyacetaldehydes, which produce hydrobenzofuranones via asymmetric intramolecular Stetter reaction in good to excellent yield. Quaternary as well as up to three contiguous stereocenters may be formed in good to excellent enantioselectivities and high diastereoselectivities.
Department of Chemistry, Colorado State University, Fort Collins, 80523, USA.
Qin
Q
Liu
Tomislav
T
Rovis
D000447:Aldehydes / Q000737:chemistry; D001572:Benzofurans / Q000138:chemical synthesis*; D003500:Cyclization; D003510:Cyclohexanes / Q000737:chemistry*; D053138:Cyclohexenes
D000447:Aldehydes; D001572:Benzofurans; D003510:Cyclohexanes; D053138:Cyclohexenes; C507608:cyclohexadienone