2023
DOI: 10.1021/acs.joc.3c01885
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Regioselectivity Switch between Enantioselective 1,2- and 1,4-Addition of Allyl Aryl Ketones with 2,3-Dioxopyrrolidines

Bo-Wei Huang,
Jeng-Liang Han

Abstract: A vinylogous addition reaction of allyl aryl ketones with good yields and excellent regioselectivity catalyzed by squaramide catalysts has been developed. A series of chiral tertiary alcohols and bicyclic pyrrolidones could be synthesized in good to excellent yields, enantioselectivities, and diaseteroselectivities. Both experimental results and DFT calculations indicate that 1,2-addition reaction is favorable when the reaction is employed at a lower temperature, while the 1,4-addition/cyclization pathway is f… Show more

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Cited by 6 publications
(2 citation statements)
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“…Most of the reported methods involved an [4 + 2] annulation reaction strategy using oxidative NHC organocatalysts, amine catalysts, bifunctional amine catalysts, and phosphine catalysts . Recently, our group reported a [4 + 2] annulation reaction between 2,3-dioxopyrrolidines and allyl aryl ketones catalyzed by a quinine-derived squaramide catalyst with moderate diastereoselectivity (Scheme a) . Despite several efforts being made, the development of an elegant strategy for the asymmetric synthesis of enantioenriched fused γ-lactam or pyrrolidine derivatives is still highly demand.…”
Section: Introductionmentioning
confidence: 99%
See 1 more Smart Citation
“…Most of the reported methods involved an [4 + 2] annulation reaction strategy using oxidative NHC organocatalysts, amine catalysts, bifunctional amine catalysts, and phosphine catalysts . Recently, our group reported a [4 + 2] annulation reaction between 2,3-dioxopyrrolidines and allyl aryl ketones catalyzed by a quinine-derived squaramide catalyst with moderate diastereoselectivity (Scheme a) . Despite several efforts being made, the development of an elegant strategy for the asymmetric synthesis of enantioenriched fused γ-lactam or pyrrolidine derivatives is still highly demand.…”
Section: Introductionmentioning
confidence: 99%
“… 11 Recently, our group reported a [4 + 2] annulation reaction between 2,3-dioxopyrrolidines and allyl aryl ketones catalyzed by a quinine-derived squaramide catalyst with moderate diastereoselectivity ( Scheme 1 a). 12 Despite several efforts being made, the development of an elegant strategy for the asymmetric synthesis of enantioenriched fused γ-lactam or pyrrolidine derivatives is still highly demand.…”
Section: Introductionmentioning
confidence: 99%