Diversity-oriented synthesis of chromenopyrrolidines from azomethine ylides and 2-hydroxybenzylidene indandiones via base-controlled regiodivergent (3+2) cycloaddition

Jhen Kuei Yu; Han Wei Chien; Yi Jung Lin; Praneeth Karanam; Yu Heng Chen; Wenwei Lin

doi:10.1039/c8cc05693e

Diversity-oriented synthesis of chromenopyrrolidines from azomethine ylides and 2-hydroxybenzylidene indandiones via base-controlled regiodivergent (3+2) cycloaddition

Jhen Kuei Yu
, Han Wei Chien
, Yi Jung Lin
, Praneeth Karanam
, Yu Heng Chen
, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

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

50 Citations (Scopus)

Abstract

An organobase-directed, regiodivergent 1,3-dipolar cycloaddition of azomethine ylides and 2-hydoxybenzylidene indandiones is reported. The scarcely explored reversal of the nucleophilic site in azomethine ylides has been exploited for their regiodivergent (3+2) cycloaddition, which subsequently resulted in two different cascade processes to generate functionally distinct chromenopyrrolidines in a diversity oriented manner.

Original language	English
Pages (from-to)	9921-9924
Number of pages	4
Journal	Chemical Communications
Volume	54
Issue number	71
DOIs	https://doi.org/10.1039/c8cc05693e
Publication status	Published - 2018

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c8cc05693e

Cite this

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title = "Diversity-oriented synthesis of chromenopyrrolidines from azomethine ylides and 2-hydroxybenzylidene indandiones via base-controlled regiodivergent (3+2) cycloaddition",

abstract = "An organobase-directed, regiodivergent 1,3-dipolar cycloaddition of azomethine ylides and 2-hydoxybenzylidene indandiones is reported. The scarcely explored reversal of the nucleophilic site in azomethine ylides has been exploited for their regiodivergent (3+2) cycloaddition, which subsequently resulted in two different cascade processes to generate functionally distinct chromenopyrrolidines in a diversity oriented manner.",

author = "Yu, \{Jhen Kuei\} and Chien, \{Han Wei\} and Lin, \{Yi Jung\} and Praneeth Karanam and Chen, \{Yu Heng\} and Wenwei Lin",

note = "Publisher Copyright: {\textcopyright} 2018 The Royal Society of Chemistry.",

year = "2018",

doi = "10.1039/c8cc05693e",

language = "English",

volume = "54",

pages = "9921--9924",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "71",

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T1 - Diversity-oriented synthesis of chromenopyrrolidines from azomethine ylides and 2-hydroxybenzylidene indandiones via base-controlled regiodivergent (3+2) cycloaddition

AU - Yu, Jhen Kuei

AU - Chien, Han Wei

AU - Lin, Yi Jung

AU - Karanam, Praneeth

AU - Chen, Yu Heng

AU - Lin, Wenwei

PY - 2018

Y1 - 2018

N2 - An organobase-directed, regiodivergent 1,3-dipolar cycloaddition of azomethine ylides and 2-hydoxybenzylidene indandiones is reported. The scarcely explored reversal of the nucleophilic site in azomethine ylides has been exploited for their regiodivergent (3+2) cycloaddition, which subsequently resulted in two different cascade processes to generate functionally distinct chromenopyrrolidines in a diversity oriented manner.

AB - An organobase-directed, regiodivergent 1,3-dipolar cycloaddition of azomethine ylides and 2-hydoxybenzylidene indandiones is reported. The scarcely explored reversal of the nucleophilic site in azomethine ylides has been exploited for their regiodivergent (3+2) cycloaddition, which subsequently resulted in two different cascade processes to generate functionally distinct chromenopyrrolidines in a diversity oriented manner.

UR - https://www.scopus.com/pages/publications/85052740941

UR - https://www.scopus.com/pages/publications/85052740941#tab=citedBy

U2 - 10.1039/c8cc05693e

DO - 10.1039/c8cc05693e

M3 - Article

C2 - 30116804

AN - SCOPUS:85052740941

SN - 1359-7345

VL - 54

SP - 9921

EP - 9924

JO - Chemical Communications

JF - Chemical Communications

IS - 71

ER -

Diversity-oriented synthesis of chromenopyrrolidines from azomethine ylides and 2-hydroxybenzylidene indandiones via base-controlled regiodivergent (3+2) cycloaddition

Abstract

ASJC Scopus subject areas

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CCDC 1551248: Experimental Crystal Structure Determination

CCDC 1551249: Experimental Crystal Structure Determination

CCDC 1841899: Experimental Crystal Structure Determination

Cite this

Diversity-oriented synthesis of chromenopyrrolidines from azomethine ylides and 2-hydroxybenzylidene indandiones via base-controlled regiodivergent (3+2) cycloaddition

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1551248: Experimental Crystal Structure Determination

CCDC 1551249: Experimental Crystal Structure Determination

CCDC 1841899: Experimental Crystal Structure Determination

Cite this