Calcium(II)- and Triflimide-Catalyzed Intramolecular Hydroacyloxylation of Unactivated Alkenes in Hexafluoroisopropanol

Authors :: David Lebœuf
Vincent Gandon
Shengwen Yang
Chenxiao Qi
Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO)
Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
Laboratoire de chimie moléculaire (LCM)
Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-École polytechnique (X)
Source :: Organic Letters, Organic Letters, American Chemical Society, 2019, 21 (18), pp.7405-7409. ⟨10.1021/acs.orglett.9b02705⟩
Publication Year :: 2019
Publisher :: American Chemical Society (ACS), 2019.
Abstract: We report an efficient intramolecular hydroacyloxylation of unactivated alkenes, offering a streamlined access to relevant γ-lactones, which features the utilization of either a calcium(II) salt or triflimide as a catalyst in hexafluoroisopropanol. This method could be applied to the synthesis of natural products and the late-stage functionalization of natural and bioactive molecules. Additionally, DFT computations were used to elucidate the twist of reactivity observed between the hydroamidation and hydroacyloxylation of unactivated alkenes regarding the formation of 5- and 6-membered rings.

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