Diastereoselective Synthesis of Rauhut-Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives

Shu Mei Yang; Ganapuram Madhusudhan Reddy; Meng Hsien Liu; Tzu Ping Wang; Jhen Kuei Yu; Wenwei Lin

doi:10.1021/acs.joc.6b02526

Diastereoselective Synthesis of Rauhut-Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives

Shu Mei Yang, Ganapuram Madhusudhan Reddy, Meng Hsien Liu, Tzu Ping Wang, Jhen Kuei Yu, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

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

21 Citations (Scopus)

Abstract

A novel, base-catalyzed and highly diastereoselective direct Michael addition-isomerization sequence is presented for the efficient synthesis of Rauhut-Currier-type adducts. An unexpected α-addition of γ-butyrolactam onto the 3-acyl coumarin derivatives was observed rather than the γ-addition, which is more common. The adducts could further undergo hydrolysis/decarboxylation to generate the products which are equivalent to those obtained by α-addition of γ-butyrolactam onto the corresponding chalcones.

Original language	English
Pages (from-to)	781-789
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	82
Issue number	1
DOIs	https://doi.org/10.1021/acs.joc.6b02526
Publication status	Published - 2017 Jan 6

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.6b02526

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@article{3f4c9f162ebd40a092e836b3535174cd,

title = "Diastereoselective Synthesis of Rauhut-Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives",

abstract = "A novel, base-catalyzed and highly diastereoselective direct Michael addition-isomerization sequence is presented for the efficient synthesis of Rauhut-Currier-type adducts. An unexpected α-addition of γ-butyrolactam onto the 3-acyl coumarin derivatives was observed rather than the γ-addition, which is more common. The adducts could further undergo hydrolysis/decarboxylation to generate the products which are equivalent to those obtained by α-addition of γ-butyrolactam onto the corresponding chalcones.",

author = "Yang, {Shu Mei} and {Madhusudhan Reddy}, Ganapuram and Liu, {Meng Hsien} and Wang, {Tzu Ping} and Yu, {Jhen Kuei} and Wenwei Lin",

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

year = "2017",

month = jan,

day = "6",

doi = "10.1021/acs.joc.6b02526",

language = "English",

volume = "82",

pages = "781--789",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - Diastereoselective Synthesis of Rauhut-Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives

AU - Yang, Shu Mei

AU - Madhusudhan Reddy, Ganapuram

AU - Liu, Meng Hsien

AU - Wang, Tzu Ping

AU - Yu, Jhen Kuei

AU - Lin, Wenwei

PY - 2017/1/6

Y1 - 2017/1/6

N2 - A novel, base-catalyzed and highly diastereoselective direct Michael addition-isomerization sequence is presented for the efficient synthesis of Rauhut-Currier-type adducts. An unexpected α-addition of γ-butyrolactam onto the 3-acyl coumarin derivatives was observed rather than the γ-addition, which is more common. The adducts could further undergo hydrolysis/decarboxylation to generate the products which are equivalent to those obtained by α-addition of γ-butyrolactam onto the corresponding chalcones.

AB - A novel, base-catalyzed and highly diastereoselective direct Michael addition-isomerization sequence is presented for the efficient synthesis of Rauhut-Currier-type adducts. An unexpected α-addition of γ-butyrolactam onto the 3-acyl coumarin derivatives was observed rather than the γ-addition, which is more common. The adducts could further undergo hydrolysis/decarboxylation to generate the products which are equivalent to those obtained by α-addition of γ-butyrolactam onto the corresponding chalcones.

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AN - SCOPUS:85018506638

SN - 0022-3263

VL - 82

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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Diastereoselective Synthesis of Rauhut-Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives

Abstract

ASJC Scopus subject areas

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CCDC 1485688: Experimental Crystal Structure Determination

CCDC 1037980: Experimental Crystal Structure Determination

CCDC 1401267: Experimental Crystal Structure Determination

Cite this

Diastereoselective Synthesis of Rauhut-Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1485688: Experimental Crystal Structure Determination

CCDC 1037980: Experimental Crystal Structure Determination

CCDC 1401267: Experimental Crystal Structure Determination

Cite this