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Highly Enantioselective [3 + 2] Annulation of 3‑Butynoates with β‑Trifluoromethyl Enones Promoted by an Amine−Phosphine Binary Catalytic System
journal contribution
posted on 2020-03-10, 16:54 authored by Huanzhen Ni, Yee Lin Wong, Mingyue Wu, Zhaobin Han, Kuiling Ding, Yixin LuWe report a highly
enantioselective [3 + 2] annulation between
3-butynoates and β-trifluoromethyl enones, furnishing trifluoromethylated
cyclopentenes with three contiguous stereogenic centers in good yields,
high diastereoselectivities, and excellent enantioselectivities. A
unique catalytic system consisting of a simple amine and a chiral
phosphine was devised, and the synergistic play of Lewis basic amine
and phosphine was crucial for alkyne isomerization and subsequent
cyclization. The protocol disclosed herein allows facile activation
of 3-butynoates in phosphine-mediated asymmetric transformations.
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EnantioselectiveannulationCatalyticAnnulationphosphine-mediatedButynoatediastereoselectivitieenantioselectivecyclization3- butynoatesTrifluoromethylactivationEnoneenantioselectivitiealkynefurnishing trifluoromethylated cyclopentenesphosphinePromotedchiralcenterβ- trifluoromethyl enonesstereogenicLewisyieldtransformationAmineisomerizationamine
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