Switchable pyrrole-based hydrogen bonding motif in enantioselective trifunctional organocatalysis

Sviatoslav S. Eliseenko; Fei Liu

doi:10.1016/j.tet.2018.12.016

Switchable pyrrole-based hydrogen bonding motif in enantioselective trifunctional organocatalysis

Sviatoslav S. Eliseenko, Fei Liu^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

Pyrroles are versatile chemical motifs for molecular recognition or ligand design but their utility as catalytic components are underexplored. We incorporated a pyrrole motif into our acid-switchable, MAP-based trifunctional organocatalytic system. The switching-on of this system by an external Brønsted acid, 3-methyl benzoic acid, presented proficient catalysis in both aza-Morita–Baylis–Hillman (MBH, up to >95% conversion and 88% ee over 3 h) and MBH (up to 81% conversion and 77% ee over 6 h) reactions. The enhanced catalytic generality and proficiency may be due to the new cooperativity via CH/π interactions between pyrrole and the acid switch.

Original language	English
Pages (from-to)	518-526
Number of pages	9
Journal	Tetrahedron
Volume	75
Issue number	4
DOIs	https://doi.org/10.1016/j.tet.2018.12.016
Publication status	Published - 25 Jan 2019

Keywords

Switchable catalysis
Cooperativity
Trifunctional organocatalysis
Enantioselectivity
Pyrroles
Moritae-Baylise-Hillman reaction

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10.1016/j.tet.2018.12.016

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title = "Switchable pyrrole-based hydrogen bonding motif in enantioselective trifunctional organocatalysis",

abstract = "Pyrroles are versatile chemical motifs for molecular recognition or ligand design but their utility as catalytic components are underexplored. We incorporated a pyrrole motif into our acid-switchable, MAP-based trifunctional organocatalytic system. The switching-on of this system by an external Br{\o}nsted acid, 3-methyl benzoic acid, presented proficient catalysis in both aza-Morita–Baylis–Hillman (MBH, up to >95% conversion and 88% ee over 3 h) and MBH (up to 81% conversion and 77% ee over 6 h) reactions. The enhanced catalytic generality and proficiency may be due to the new cooperativity via CH/π interactions between pyrrole and the acid switch.",

keywords = "Switchable catalysis, Cooperativity, Trifunctional organocatalysis, Enantioselectivity, Pyrroles, Moritae-Baylise-Hillman reaction",

author = "Eliseenko, {Sviatoslav S.} and Fei Liu",

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language = "English",

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journal = "Tetrahedron",

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TY - JOUR

T1 - Switchable pyrrole-based hydrogen bonding motif in enantioselective trifunctional organocatalysis

AU - Eliseenko, Sviatoslav S.

AU - Liu, Fei

PY - 2019/1/25

Y1 - 2019/1/25

N2 - Pyrroles are versatile chemical motifs for molecular recognition or ligand design but their utility as catalytic components are underexplored. We incorporated a pyrrole motif into our acid-switchable, MAP-based trifunctional organocatalytic system. The switching-on of this system by an external Brønsted acid, 3-methyl benzoic acid, presented proficient catalysis in both aza-Morita–Baylis–Hillman (MBH, up to >95% conversion and 88% ee over 3 h) and MBH (up to 81% conversion and 77% ee over 6 h) reactions. The enhanced catalytic generality and proficiency may be due to the new cooperativity via CH/π interactions between pyrrole and the acid switch.

AB - Pyrroles are versatile chemical motifs for molecular recognition or ligand design but their utility as catalytic components are underexplored. We incorporated a pyrrole motif into our acid-switchable, MAP-based trifunctional organocatalytic system. The switching-on of this system by an external Brønsted acid, 3-methyl benzoic acid, presented proficient catalysis in both aza-Morita–Baylis–Hillman (MBH, up to >95% conversion and 88% ee over 3 h) and MBH (up to 81% conversion and 77% ee over 6 h) reactions. The enhanced catalytic generality and proficiency may be due to the new cooperativity via CH/π interactions between pyrrole and the acid switch.

KW - Switchable catalysis

KW - Cooperativity

KW - Trifunctional organocatalysis

KW - Enantioselectivity

KW - Pyrroles

KW - Moritae-Baylise-Hillman reaction

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U2 - 10.1016/j.tet.2018.12.016

DO - 10.1016/j.tet.2018.12.016

M3 - Article

AN - SCOPUS:85058946150

VL - 75

SP - 518

EP - 526

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 4

ER -

Switchable pyrrole-based hydrogen bonding motif in enantioselective trifunctional organocatalysis

Abstract

Keywords

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