Alkylidene Meldrum′s Acid as Acceptor-Donor-Acceptor with Azomethine Ylide for Organocatalytic Asymmetric (3+2) Cycloaddition/Annulation: Synthesis of Chromeno[4,3-b]pyrrolidine

Yan Cheng Liou; Yi Ru Chen; Ching Wen Hsu; Xuan Rui Huang; Heng Wei Wang; Wenwei Lin

doi:10.1002/adsc.202300609

Alkylidene Meldrum′s Acid as Acceptor-Donor-Acceptor with Azomethine Ylide for Organocatalytic Asymmetric (3+2) Cycloaddition/Annulation: Synthesis of Chromeno[4,3-b]pyrrolidine

Yan Cheng Liou, Yi Ru Chen, Ching Wen Hsu, Xuan Rui Huang, Heng Wei Wang, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

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

Abstract

A quinine-derived thiourea-catalyzed enantioselective double annulation strategy using alkylidene Meldrum′s acid as an acceptor-donor-acceptor with salicylaldehyde-derived azomethine ylide is reported. The methodology is realized via a (3+2) cycloaddition/transesterification/decarboxylation sequence, giving chromeno[4,3-b]pyrrolidines within 15–420 minutes at room temperature in 51–97% yields with 92–99% ee under 1–10 mol% catalyst loading. A plausible activation model is proposed for the excellent stereoinduction by H-bond interaction between the catalyst and the Meldrum′s acid motif according to control experiments.

Original language	English
Pages (from-to)	3603-3610
Number of pages	8
Journal	Advanced Synthesis and Catalysis
Volume	365
Issue number	21
DOIs	https://doi.org/10.1002/adsc.202300609
Publication status	Published - 2023 Nov 7

Keywords

Annulation
Asymmetric synthesis
Azomethine ylides
Meldrum′s acid
Organocatalysis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.202300609

CCDC 2081719: Experimental Crystal Structure Determination
Liou, Y. (Contributor), Chen, Y. (Contributor), Hsu, C. (Contributor), Huang, X. (Contributor), Wang, H. (Contributor) & Lin, W. (Contributor), Cambridge Crystallographic Data Centre, 2023
DOI: 10.5517/ccdc.csd.cc27w67l, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc27w67l&sid=DataCite
Dataset
CCDC 2085214: Experimental Crystal Structure Determination
Liou, Y. (Contributor), Chen, Y. (Contributor), Hsu, C. (Contributor), Huang, X. (Contributor), Wang, H. (Contributor) & Lin, W. (Contributor), Cambridge Crystallographic Data Centre, 2023
DOI: 10.5517/ccdc.csd.cc27ztz1, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc27ztz1&sid=DataCite
Dataset
CCDC 2235973: Experimental Crystal Structure Determination
Liou, Y. (Contributor), Chen, Y. (Contributor), Hsu, C. (Contributor), Huang, X. (Contributor), Wang, H. (Contributor) & Lin, W. (Contributor), Cambridge Crystallographic Data Centre, 2023
DOI: 10.5517/ccdc.csd.cc2f1q5d, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2f1q5d&sid=DataCite
Dataset

Cite this

Alkylidene Meldrum′s Acid as Acceptor-Donor-Acceptor with Azomethine Ylide for Organocatalytic Asymmetric (3+2) Cycloaddition/Annulation: Synthesis of Chromeno[4,3-b]pyrrolidine. / Liou, Yan Cheng; Chen, Yi Ru; Hsu, Ching Wen et al.
In: Advanced Synthesis and Catalysis, Vol. 365, No. 21, 07.11.2023, p. 3603-3610.

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

@article{e253d617b09e475386d2f44ff5a01222,

title = "Alkylidene Meldrum′s Acid as Acceptor-Donor-Acceptor with Azomethine Ylide for Organocatalytic Asymmetric (3+2) Cycloaddition/Annulation: Synthesis of Chromeno[4,3-b]pyrrolidine",

abstract = "A quinine-derived thiourea-catalyzed enantioselective double annulation strategy using alkylidene Meldrum′s acid as an acceptor-donor-acceptor with salicylaldehyde-derived azomethine ylide is reported. The methodology is realized via a (3+2) cycloaddition/transesterification/decarboxylation sequence, giving chromeno[4,3-b]pyrrolidines within 15–420 minutes at room temperature in 51–97% yields with 92–99% ee under 1–10 mol% catalyst loading. A plausible activation model is proposed for the excellent stereoinduction by H-bond interaction between the catalyst and the Meldrum′s acid motif according to control experiments.",

keywords = "Annulation, Asymmetric synthesis, Azomethine ylides, Meldrum′s acid, Organocatalysis",

author = "Liou, {Yan Cheng} and Chen, {Yi Ru} and Hsu, {Ching Wen} and Huang, {Xuan Rui} and Wang, {Heng Wei} and Wenwei Lin",

note = "Publisher Copyright: {\textcopyright} 2023 Wiley-VCH GmbH.",

year = "2023",

month = nov,

day = "7",

doi = "10.1002/adsc.202300609",

language = "English",

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T1 - Alkylidene Meldrum′s Acid as Acceptor-Donor-Acceptor with Azomethine Ylide for Organocatalytic Asymmetric (3+2) Cycloaddition/Annulation

T2 - Synthesis of Chromeno[4,3-b]pyrrolidine

AU - Liou, Yan Cheng

AU - Chen, Yi Ru

AU - Hsu, Ching Wen

AU - Huang, Xuan Rui

AU - Wang, Heng Wei

AU - Lin, Wenwei

PY - 2023/11/7

Y1 - 2023/11/7

N2 - A quinine-derived thiourea-catalyzed enantioselective double annulation strategy using alkylidene Meldrum′s acid as an acceptor-donor-acceptor with salicylaldehyde-derived azomethine ylide is reported. The methodology is realized via a (3+2) cycloaddition/transesterification/decarboxylation sequence, giving chromeno[4,3-b]pyrrolidines within 15–420 minutes at room temperature in 51–97% yields with 92–99% ee under 1–10 mol% catalyst loading. A plausible activation model is proposed for the excellent stereoinduction by H-bond interaction between the catalyst and the Meldrum′s acid motif according to control experiments.

AB - A quinine-derived thiourea-catalyzed enantioselective double annulation strategy using alkylidene Meldrum′s acid as an acceptor-donor-acceptor with salicylaldehyde-derived azomethine ylide is reported. The methodology is realized via a (3+2) cycloaddition/transesterification/decarboxylation sequence, giving chromeno[4,3-b]pyrrolidines within 15–420 minutes at room temperature in 51–97% yields with 92–99% ee under 1–10 mol% catalyst loading. A plausible activation model is proposed for the excellent stereoinduction by H-bond interaction between the catalyst and the Meldrum′s acid motif according to control experiments.

KW - Annulation

KW - Asymmetric synthesis

KW - Azomethine ylides

KW - Meldrum′s acid

KW - Organocatalysis

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Alkylidene Meldrum′s Acid as Acceptor-Donor-Acceptor with Azomethine Ylide for Organocatalytic Asymmetric (3+2) Cycloaddition/Annulation: Synthesis of Chromeno[4,3-b]pyrrolidine

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Datasets

CCDC 2081719: Experimental Crystal Structure Determination

CCDC 2085214: Experimental Crystal Structure Determination

CCDC 2235973: Experimental Crystal Structure Determination

Cite this