Sustainable access to benzothiophene derivatives bearing a trifluoromethyl group <i>via</i> a three-component domino reaction in water

The asymmetric γ‐regioselective‐alkylation reaction which is catalyzed by a chiral tertiary amine ((DHQ)2PHAL) and takes advantage of isatin‐derived Morita‐Baylis‐Hillman carbonates and CF3‐contained ketoimines, delivered chiral α‐trifluoromethylamine derivatives and incorporated an oxindole motif in yields of 65–98%, diastereoselectivities (>20:1 in most cases) and enantioselectivities of 73–99%. The subsequent deprotection gave α‐ trifluoromethyl amines in a stereoselective manner. Furthermore, fused polycyclic frameworks can be furnished by subsequent derivatization of the product without eroding its stereoselectivity.

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Organocatalytic Asymmetric Synthesis of α‐Trifluoromethyl Homoallylic Amine Derivatives from Trifluoromethyl‐Containing Ketoimines and Isatin‐Derived Morita‐Baylis‐Hillman Carbonates

Chen

Deng

Sun

et al. 2023

Adv Synth Catal

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Recent advances in the synthesis of trifluoromethyl-containing heterocyclic compounds via trifluoromethyl building blocks

Liu,

Tian,

et al. 2024

Org. Biomol. Chem.

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A facile access to aliphatic trifluoromethyl ketones via photocatalyzed cross-coupling of bromotrifluoroacetone and alkenes

Mizuta,

Yamaguchi,

Iwasaki

et al. 2024

Org. Biomol. Chem.

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Sustainable access to benzothiophene derivatives bearing a trifluoromethyl group via a three-component domino reaction in water

Abstract: A catalyst-free three component domino reaction was developed for the synthesis of benzothiophene fused pyrrolidones bearing a CF3 group for the first time. The notable advantages of this strategy over...

Cited by 3 publications

References 63 publications

Organocatalytic Asymmetric Synthesis of α‐Trifluoromethyl Homoallylic Amine Derivatives from Trifluoromethyl‐Containing Ketoimines and Isatin‐Derived Morita‐Baylis‐Hillman Carbonates

Organocatalytic Asymmetric Synthesis of α‐Trifluoromethyl Homoallylic Amine Derivatives from Trifluoromethyl‐Containing Ketoimines and Isatin‐Derived Morita‐Baylis‐Hillman Carbonates

Recent advances in the synthesis of trifluoromethyl-containing heterocyclic compounds via trifluoromethyl building blocks

A facile access to aliphatic trifluoromethyl ketones via photocatalyzed cross-coupling of bromotrifluoroacetone and alkenes

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