Organocatalytic enantioselective direct vinylogous michael addition of γ-substituted butenolides to 3-aroyl acrylates and 1,2-diaroylethylenes

Utpal Das; Yi Ru Chen; Yi Ling Tsai; Wen-Wei Lin

doi:10.1002/chem.201301332

Organocatalytic enantioselective direct vinylogous michael addition of γ-substituted butenolides to 3-aroyl acrylates and 1,2-diaroylethylenes

Utpal Das, Yi Ru Chen, Yi Ling Tsai, Wen-Wei Lin

Department of Chemistry

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

51 Citations (Scopus)

Abstract

Adding value: The direct vinylogous Michael addition of γ-substituted butenolides with a series of 3-aroyl acrylates and 1,2-diaroylethylenes has been demonstrated. This organocatalytic method delivers highly enantio- and diastereomerically pure γ,γ-disubstituted butenolides with adjacent quaternary and tertiary stereocenters (see scheme).

Original language	English
Pages (from-to)	7713-7717
Number of pages	5
Journal	Chemistry - A European Journal
Volume	19
Issue number	24
DOIs	https://doi.org/10.1002/chem.201301332
Publication status	Published - 2013 Jun 10

Keywords

Michael addition
cinchona alkaloids
organocatalysis
quaternary stereogenic center
γ-butenolides

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/chem.201301332

Cite this

@article{a478b806c12240a5a8f2f8eb7111691a,

title = "Organocatalytic enantioselective direct vinylogous michael addition of γ-substituted butenolides to 3-aroyl acrylates and 1,2-diaroylethylenes",

abstract = "Adding value: The direct vinylogous Michael addition of γ-substituted butenolides with a series of 3-aroyl acrylates and 1,2-diaroylethylenes has been demonstrated. This organocatalytic method delivers highly enantio- and diastereomerically pure γ,γ-disubstituted butenolides with adjacent quaternary and tertiary stereocenters (see scheme).",

keywords = "Michael addition, cinchona alkaloids, organocatalysis, quaternary stereogenic center, γ-butenolides",

author = "Utpal Das and Chen, {Yi Ru} and Tsai, {Yi Ling} and Wen-Wei Lin",

year = "2013",

month = jun,

day = "10",

doi = "10.1002/chem.201301332",

language = "English",

volume = "19",

pages = "7713--7717",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "24",

}

TY - JOUR

T1 - Organocatalytic enantioselective direct vinylogous michael addition of γ-substituted butenolides to 3-aroyl acrylates and 1,2-diaroylethylenes

AU - Das, Utpal

AU - Chen, Yi Ru

AU - Tsai, Yi Ling

AU - Lin, Wen-Wei

PY - 2013/6/10

Y1 - 2013/6/10

N2 - Adding value: The direct vinylogous Michael addition of γ-substituted butenolides with a series of 3-aroyl acrylates and 1,2-diaroylethylenes has been demonstrated. This organocatalytic method delivers highly enantio- and diastereomerically pure γ,γ-disubstituted butenolides with adjacent quaternary and tertiary stereocenters (see scheme).

AB - Adding value: The direct vinylogous Michael addition of γ-substituted butenolides with a series of 3-aroyl acrylates and 1,2-diaroylethylenes has been demonstrated. This organocatalytic method delivers highly enantio- and diastereomerically pure γ,γ-disubstituted butenolides with adjacent quaternary and tertiary stereocenters (see scheme).

KW - Michael addition

KW - cinchona alkaloids

KW - organocatalysis

KW - quaternary stereogenic center

KW - γ-butenolides

UR - http://www.scopus.com/inward/record.url?scp=84878598084&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84878598084&partnerID=8YFLogxK

U2 - 10.1002/chem.201301332

DO - 10.1002/chem.201301332

M3 - Article

C2 - 23649965

AN - SCOPUS:84878598084

VL - 19

SP - 7713

EP - 7717

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 24

ER -

Organocatalytic enantioselective direct vinylogous michael addition of γ-substituted butenolides to 3-aroyl acrylates and 1,2-diaroylethylenes

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this