Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives

Geng Hua Chang; Chein Yi Wang; G. Madhusudhan Reddy; Yi Ling Tsai; Wenwei Lin

doi:10.1021/acs.joc.6b02041

Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives

Geng Hua Chang
, Chein Yi Wang
, G. Madhusudhan Reddy
, Yi Ling Tsai
, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

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

20 Citations (Scopus)

Abstract

An enantioselective synthesis of benzopyrano[3,4-c]pyrrolidine derivatives via organocatalyzed [3 + 2] cycloaddition has been achieved. Cinchona alkaloid-derived organocatalysts as Brønsted bases have been examined for this asymmetric cycloaddition of o-hydroxy aromatic aldimines with 3-substituted coumarins. An unexpected rearrangement of the quaternary acyl moiety in the products resulted in an in situ protection of the o-hydroxy group.

Original language	English
Pages (from-to)	10071-10080
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	81
Issue number	20
DOIs	https://doi.org/10.1021/acs.joc.6b02041
Publication status	Published - 2016 Oct 21

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.6b02041

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Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives. / Chang, Geng Hua; Wang, Chein Yi; Madhusudhan Reddy, G. et al.
In: Journal of Organic Chemistry, Vol. 81, No. 20, 21.10.2016, p. 10071-10080.

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

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title = "Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives",

abstract = "An enantioselective synthesis of benzopyrano[3,4-c]pyrrolidine derivatives via organocatalyzed [3 + 2] cycloaddition has been achieved. Cinchona alkaloid-derived organocatalysts as Br{\o}nsted bases have been examined for this asymmetric cycloaddition of o-hydroxy aromatic aldimines with 3-substituted coumarins. An unexpected rearrangement of the quaternary acyl moiety in the products resulted in an in situ protection of the o-hydroxy group.",

author = "Chang, \{Geng Hua\} and Wang, \{Chein Yi\} and \{Madhusudhan Reddy\}, G. and Tsai, \{Yi Ling\} and Wenwei Lin",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

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day = "21",

doi = "10.1021/acs.joc.6b02041",

language = "English",

volume = "81",

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AU - Chang, Geng Hua

AU - Wang, Chein Yi

AU - Madhusudhan Reddy, G.

AU - Tsai, Yi Ling

AU - Lin, Wenwei

PY - 2016/10/21

Y1 - 2016/10/21

N2 - An enantioselective synthesis of benzopyrano[3,4-c]pyrrolidine derivatives via organocatalyzed [3 + 2] cycloaddition has been achieved. Cinchona alkaloid-derived organocatalysts as Brønsted bases have been examined for this asymmetric cycloaddition of o-hydroxy aromatic aldimines with 3-substituted coumarins. An unexpected rearrangement of the quaternary acyl moiety in the products resulted in an in situ protection of the o-hydroxy group.

AB - An enantioselective synthesis of benzopyrano[3,4-c]pyrrolidine derivatives via organocatalyzed [3 + 2] cycloaddition has been achieved. Cinchona alkaloid-derived organocatalysts as Brønsted bases have been examined for this asymmetric cycloaddition of o-hydroxy aromatic aldimines with 3-substituted coumarins. An unexpected rearrangement of the quaternary acyl moiety in the products resulted in an in situ protection of the o-hydroxy group.

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UR - https://www.scopus.com/pages/publications/84992388881#tab=citedBy

U2 - 10.1021/acs.joc.6b02041

DO - 10.1021/acs.joc.6b02041

M3 - Article

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SN - 0022-3263

VL - 81

SP - 10071

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 20

ER -

Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives

Abstract

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CCDC 1495672: Experimental Crystal Structure Determination

CCDC 1495671: Experimental Crystal Structure Determination

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Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives

Abstract

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Datasets

CCDC 1495672: Experimental Crystal Structure Determination

CCDC 1495671: Experimental Crystal Structure Determination

Cite this