Elucidating the mechanism and regioselectivity of phosphine-catalyzed transformation of MBH carbonate

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(35), P. 16636 - 16642

Published: Jan. 1, 2023

A general mechanistic map of the PPh 3 -catalyzed transformation reaction MBH carbonate has been theoretically studied and NCI ELF analyses are performed to disclose origins selectivities role catalyst, respectively.

Language: Английский

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Chiral Phosphine Catalyzed Allylic Alkylation of Benzylidene Succinimides with Morita–Baylis–Hillman Carbonates

Molecules, Journal Year: 2023, Volume and Issue: 28(6), P. 2825 - 2825

Published: March 21, 2023

Owing to their unique chemical properties, α-alkylidene succinimides generally act as versatile synthons in organic synthesis. Compared with well-established annulations, nucleophilic alkylations of are very limited. Accordingly, an organocatalytic allylic alkylation α-benzylidene Morita–Baylis–Hillman (MBH) carbonates was established. In the presence a chiral phosphine catalyst, reacted smoothly MBH under mild conditions furnish series optical active high yields and enantioselectivities. Different from reported results, enantioselective construction pyrrolidine-2,5-dione frameworks bearing contiguous tertiary carbon centers achieved via this synthetic strategy. Scaling up reaction indicated that it is practical strategy for succinimides. A possible mechanism also proposed.

Language: Английский

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Enantioselective Synthesis of 3‐Allylindoles from Indolin‐2‐imines and MBH Carbonates via Nucleophilic Catalysis

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(6)

Published: Feb. 7, 2024

Abstract With chiral amine (DHQD) 2 PHAL as nucleophilic catalyst, asymmetric synthesis of enantioenriched 3‐allylindoles was achieved from indolone‐2‐imines and MBH carbonates. Compared with our previous phosphine catalysis, the had exactly opposite effect in terms enantioselectivity. Importantly, we could obtain each enantiomer by adjusting catalyst system.

Language: Английский

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Organocatalytic Stereodivergent Dearomatization and N-Acylation of 2-Amino-3-subsituted Indoles

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 5, 2024

Organocatalytic chemo- and enantioselective reactions of 2-amino-3-subsituted indoles have been achieved for the first time. Via asymmetric allylic alkylation Morita-Baylis-Hillman carbonates, organocatalytic dearomatization afforded an array enantioenriched 3,3-disubstituted indolin-2-imines bearing a quaternary carbon stereocenter in 34-79% yields with 61-91% ee. With Boc

Language: Английский

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Eco-friendly K-10 Clay-Mediated [3 + 3] Spiroannulation of Morita–Baylis–Hillman Adduct of Isatin with Anthracene: Synthesis of Green Fluorophore Compounds

ACS Omega, Journal Year: 2023, Volume and Issue: 9(1), P. 934 - 941

Published: Dec. 20, 2023

An easy and simple spiroannulation of the Morita–Baylis–Hillman adduct isatin derivatives with anthracene was achieved in moderate-to-good yields (37–75%). The spiroderivatives synthesized this work exhibited green fluorescence properties. reaction occurred metal-free eco-friendly K-10 clay-mediated conditions. final products have multiple structural features such as 3-spirooxindole, fluorophoric anthracene, phenanthracene, phenalene, perylene cores.

Language: Английский

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DABCO-catalyzed mono- and bisallylation of β,γ-unsaturated ketones with Morita-Baylis-Hillman carbonates

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(35), P. 15446 - 15451

Published: Jan. 1, 2024

Mono- and bisallylation of β,γ-unsaturated ketones with MBH carbonates in the presence DABCO at rt, offered α-2-alkoxycarbonyl, α,α-di(2-alkoxycarbonyl) α,γ-di(2-alkoxycarbonyl) α,β-unsaturated moderate to excellent yields.

Language: Английский

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